REARRANGEMENT STUDIES WITH C14: XII. THE REACTION OF NITROUS ACID WITH 2-α- OR 2-β-NAPHTHYLETHYLAMINE-1-C14

1962 ◽  
Vol 40 (6) ◽  
pp. 1130-1133
Author(s):  
A. G. Forman ◽  
C. C. Lee
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Sodium Nitrite ◽  
Nitrous Acid ◽  
Glacial Acetic Acid ◽  
Aqueous Hydrochloric Acid

On treatment with sodium nitrite, 2-α-naphthylethylamine-1-C14 in aqueous hydrochloric acid or glacial acetic acid gives rise to the corresponding alcohol, which shows rearrangement of C14 from the C-1 to the C-2 positions to the extent of 32–35%; the 2-β-naphthyl isomer exhibits 26–28% rearrangement. The significance of these results is discussed.

REARRANGEMENT IN THE REACTION BETWEEN 2-PHENYLETHYLAMINE-1-C14 AND NITROUS ACID

1953 ◽  
Vol 31 (8) ◽  
pp. 761-767 ◽  
Author(s):  
C. C. Lee ◽  
J. W. T. Spinks
Keyword(s):  
Acetic Acid ◽  
Sodium Nitrite ◽  
Nitrous Acid ◽  
Glacial Acetic Acid ◽  
Reaction Intermediates ◽  
Carbonium Ions

On treatment with sodium nitrite, 2-phenylethylamine-1-C14 in aqueous hydrochloric, perchloric, acetic, or glacial acetic acid gives rise to products in which the C14 atoms have been rearranged from the C-1 to the C-2 position to an extent of 20.5 to 22.5%. The results are discussed on the basis of carbonium ions as possible reaction intermediates.

PHTHALIDE FORMATION: IV. CONDENSATIONS WITH 5-METHOXY-3-METHYLBENZOIC ACID

1963 ◽  
Vol 41 (5) ◽  
pp. 1071-1077 ◽  
Author(s):  
E. H. Charlesworth ◽  
Leon Levene
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Glacial Acetic Acid ◽  
Heating Period ◽  
Short Period ◽  
Aqueous Formaldehyde

The products of the condensation of 5-methoxy-3-methylbenzoic acid with aqueous formaldehyde and hydrochloric acid in the presence of glacial acetic acid are dependent on the length of the heating period. A very short period of heating (2 minutes) yields 6-methoxy-4-methylphthalide and the two chloromethylphthalides of m.p. 135° and 154 °C, related to the unisolated 4-methoxy-6-methylphthalide. If the period of heating is 20 minutes or longer, the above chloromethylphthalide melting at 135° is formed and in addition some of the 6-methoxy-4-methylphthalide is chloromethylated to 6-methoxy-7-chloromethyl-4-methylphthalide, melting at 179°. The orientation of all three chloromethylphthalides has been established.

Synthesis of Three Different Types of Chalcone Derivatives

2014 ◽  
Vol 1033-1034 ◽  
pp. 81-84
Author(s):  
He Ping Yan ◽  
Du Shu Huang ◽  
Ju Cheng Zhang ◽  
Rui Na Huang ◽  
You Wang Fu ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Room Temperature ◽  
Glacial Acetic Acid ◽  
Chalcone Derivatives ◽  
Different Types ◽  
Naoh Solution

Three chalcone derivatives were synthesized by the reaction of acetophenone with dimethylamino benzaldehyde, vanillin, diphenyl formaldehyde, respectively. The results showed that: A yield of 80.4% was obtained by the reaction of acetophenone and dimethylamino benzaldehyde in ethanol as solvent, 10% NaOH solution as catalyst at room temperature. A yield of 25.0% was obtained by the reaction of acetophenone and vanillin in ethanol as solvent, a mixed glacial acetic acid and hydrochloric acid as the catalyst, adding 10% KOH solution for dehydration by heating after the reaction at room temperature. A yield of 76.3% was obtained by the reaction of acetophenone and diphenyl formaldehyde in ethanol as solvent, 10% NaOH solution as catalyst at room temperature. Acid was used as the appropriate catalyst when chalcone derivatives were synthesized by aldehyde with hydroxy.

Can Nitroalkanes be Obtained Directly from Alcohols and Sodium Nitrite in Acetic Acid - Hydrochloric Acid Mixture?

Synlett ◽  
2001 ◽  
Vol 2001 (07) ◽  
pp. 1121-1122 ◽  
Author(s):  
Mieczysław Mąkosza ◽  
Michał Barbasiewicz ◽  
Krzysztof Wojciechowski
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Sodium Nitrite ◽  
Acid Mixture

Review of Methods for Mercury in Pesticide Formulations

1969 ◽  
Vol 52 (4) ◽  
pp. 764-767
Author(s):  
James E Launer
Keyword(s):  
Acetic Acid ◽  
Hydrogen Sulfide ◽  
Hydrochloric Acid ◽  
Glacial Acetic Acid ◽  
Mercury Compounds ◽  
Pesticide Formulations ◽  
Sulfide Precipitation

Abstract Outlines are given for mercury methods that have been accepted by CIPAC. One method separates mercury from other pesticides by dissolving the pesticide in hot glacial acetic acid and amalgamating the mercury on zinc. Another method dissolves mercury in hydrochloric acid and separates it from other pesticides by hydrogen sulfide precipitation or by amalgamation on zinc. Other oxidation procedures are given for decomposition of mercury compounds. Further study is recommended for the method in which mercury is released with fuming sulfuric-nitric acids and determined with thiocyanate titration.

Rapid and Simple Determination of Oxyphenbutazone in Dosage Forms by Biamperometric Titration

1986 ◽  
Vol 69 (2) ◽  
pp. 191-192
Author(s):  
Daniela Šebková ◽  
Luděk Šafařík
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Glacial Acetic Acid ◽  
Platinum Electrode ◽  
Potassium Bromide ◽  
Dosage Forms ◽  
End Point

Abstract Oxyphenbutazone was determined in the presence of glacial acetic acid, hydrochloric acid, and potassium bromide by bromometric titration with biamperometric end point indication. The course of the titration was followed with double platinum electrode with 100 mV of polarizing voltage

scholarly journals I. Contributions to the history of the opium alkaloids.— Part V

1872 ◽  
Vol 20 (130-138) ◽  
pp. 277-289
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Glacial Acetic Acid ◽  
Ethereal Extract ◽  
Large Excess ◽  
Opium Alkaloids ◽  
Slight Excess ◽  
Secondary Reactions ◽  
History Of ◽  
Crystalline Mass

In Part IV . of these researches reasons have been adduced for the following general conclusions, viz. that codeia and morphia are capable of forming polymerides (with the elimination of methyl in the case of codeia is some instances), which yield derivatives containing certainly not less than C 68 , and probably not less than C 130 (C 72 and C 144 in the case of those codeia derivatives where methyl has not been eliminated). Experiments now in progress tend to show that the formulae of codeia and morphia are really double of those formerly ascribed to these bases i, e . are C 30 H 42 N 2 O 6 and C 30 H 42 N 2 O 6 respectively, the proof of which is (as will be shown in a subsequent communication) that the first products of the action of hydrochloric acid on these bases appear to ‘contain chlorine and carbon in the proportions C 36 and Cl, C 34 and Cl respectively, instead of C 18 and Cl, C 17 and Cl. It might be anticipated, therefore, that intermediate polymerides might be form ed containing respectively :— Morphia series. Monomorphia.. C 34 H 38 N 206 Dimorphia . . . . C 68 H 70 N 4 O 12 Trimorphia.. . . C 102 H 104 N 6 O 18 Tetramorphia.. C 136 H 152 N 8 O 24 Codeia series. C 36 H 42 N 2 O 6 . . . Monocodeia. C 72 H 84 N 4 O 12 . . Dicodeia. C 108 H 126 N 6 O 6 . . Tricodeia. C 144 H 168 N 8 O 24 . . Tetracodeia. In the case of codeia these anticipations have been verified. In order to obtain these supposed polymerides before their alteration by secondary reactions, the action of acids other than a hydro acids was examined. Acetic acid seemed a probable agent for purpose ; but no appreciable quantity of any thing different from in codeia was obtained after sixty-four hours’ digestion a t 100° of one part this base with three parts of glacial acetic acid. On precipitation of product by Na 2 CO 3 in large excess, extraction with ether, and agitation of the ethereal extract with HCl, a crystalline mass was obtained while developed a smell of acetic acid on standing in contact with a slight excess of HCl ; but on analysis this gave numbers agreeing with those required codeia hydrochlorate, and from it nothing different from codeia could't obtained ; probably therefore only a trace of acetyl-codeia was formed.

scholarly journals The Nitrous Acid Deamination of Methyl 2-Amino-2-deoxy-alpha-D-glucopyranoside, 2-Amino-2-deoxy-1,3,4,6-tetra-O-acetyl-beta-D-glucopyranose and 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosylamine in Glacial Acetic Acid.

1983 ◽  
Vol 37b ◽  
pp. 72-74 ◽  
Author(s):  
Ibrahim Gouda ◽  
Olle Larm ◽  
M. Mosihuzzaman ◽  
Dan Johnels ◽  
Sven Hellberg ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Nitrous Acid ◽  
Glacial Acetic Acid

scholarly journals SYNTHESIS OF 7-HYDROXY-2,8-DIMETHYL-4-OXO-3-PHENOXY-4H-6-CHROMENECARBALDEHYDE

2018 ◽  
pp. 54-57
Author(s):  
Т. Shokol ◽  
N. Gorbulenko ◽  
V. Khilya
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Glacial Acetic Acid ◽  
Ortho Position ◽  
Subsequent Removal ◽  
Electrophilic Attack ◽  
Reaction Conditions ◽  
Duff Reaction ◽  
The Mannich Reaction ◽  
Hydrolysis Of

Ortho-hydroxyformylchromones are convenient syntones for the construction of linear and angular hetarenochromones. Usually, 7-hydroxy-6-formylchromones were synthesized by oxidation of natural linear furochromones: visnagin and kellin and their synthetic analogues. The Duff reaction, which is the formylation of phenols in the ortho-position by heating with hexamethylenetetramine followed by acidic hydrolysis of intermediate imine, was also used to convert 7-hydroxychromones into 7-hydroxy-6-formylchromones, but in this case there were some difficulties because of the passivity of position 6 in 7-hydroxychromones compared to position 8 to the electrophilic attack. Thus, for the preparation of 7-hydroxy-6-formylchromones, it is necessary to use 8-substituted derivatives and to provide formylation for a long time.A method for the synthesis of 7-hydroxy-6-formylchromones based on 8-substituted 7-hydroxy-6-dialkylaminomethylchromones and hexamethylenetetramine was developed using the Duff reaction conditions. This method was demonstrated on the synthesis of 7-hydroxy-2,8-dimethyl-4-oxo-3-phenoxy-4H-6-chromenecarbaldehyde from 6-dimethylaminomethyl-7-hydroxy-2,8-dimethyl-3-phenoxy-4H-4-chromenone and hexamethylenetetramine in glacial acetic acid at reflux. It should be noted that when carrying out this reaction under heating on a water bath with subsequent hydrochloric acid hydrolysis only Mannich basehydrochloride was isolated from the reaction mixture. The starting 6-dimethylaminomethyl-7-hydroxy-2,8-dimethyl-3-phenoxy-4H-4-chromenone was synthesized from 1-(2,4-dihydroxy-3-methylphenyl)-2-phenoxyethanone in three steps. Acylation of the latter with acetic anhydride in the presence of triethylamine followed by condensation afforded 2,8-dimethyl-4-оxо-3-phenoxy-4Н-7-chromenylаcetate. Subsequent removal of acetyl protection resulted in 7-hydroxy-2,8-dimethyl-3-phenoxy-4H-4-chromenone, which on introduction into the Mannich reaction with bisdimethylaminomethane in dioxane gave rise to the desired 6-dimethylaminomethyl derivative.

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