265. Optical studies of 2′-substituted 2-t-butylbiphenyls. Part II. 2-Nitro-2′-t-butylbiphenyl-4-carboxylic acid and 8-o-t-butylphenyl-1-naphthoic acid

1962 ◽  
Vol 0 (0) ◽  
pp. 1401-1405 ◽  
Author(s):  
Mary S. Lesslie ◽  
Ursula J. H. Mayer
Keyword(s):  
Carboxylic Acid ◽  
Optical Studies ◽  
Naphthoic Acid

Pulse polarographic study of the behaviour of some o,o'-dihydroxyazo-compounds

1989 ◽  
Vol 54 (5) ◽  
pp. 1219-1226 ◽  
Author(s):  
Enric Casassas ◽  
Miquel Esteban ◽  
Santiago Alier
Keyword(s):  
Carboxylic Acid ◽  
Reaction Mechanisms ◽  
Sulphonic Acid ◽  
Base Catalysis ◽  
Polarographic Study ◽  
Acid Base ◽  
Eriochrome Black T ◽  
Naphthoic Acid ◽  
Calcon Carboxylic Acid

The reduction of several o,o'-dihydroxyazo-compounds is studied by means of pulse polarographic techniques (DPP, NPP and RPP). The compounds studied are the following: 2-(2'-hydroxyphenylazo)-phenol (o,o'-dihydroxyazobenzene), 1-(2'-hydroxy-1'-naphthylazo)-2-naphthol-4-sulphonic acid (calcon or Eriochrome Blue Black R), 1-(2'-hydroxy-4'-sulpho-1'-naphthylazo)-2-hydroxy-3-naphthoic acid (calcon carboxylic acid), and 1-(1'-hydroxy-2'-naphthylazo)-6-nitro-2-naphthol-4-sulphonic acid (Eriochrome Black T). Correlations between Ip and Epand experimental variables (pH, T, conc.) and instrumental parameters (dropping time, t, and pulse magnitude, ΔE) are established. Reaction mechanisms formerly proposed are discussed on the basis of the new obtained results, and the ranges are defined where adsorption and/or acid-base catalysis are operative.

Exhaustive C-methylation of carboxylic acids by trimethylaluminium: A new route to t-butyl compounds

1974 ◽  
Vol 27 (8) ◽  
pp. 1665 ◽  
Author(s):  
A Meisters ◽  
T Mole
Keyword(s):  
Carboxylic Acid ◽  
Benzoic Acid ◽  
Carboxylic Acids ◽  
Cinnamic Acid ◽  
Benzoic Acids ◽  
Naphthoic Acid ◽  
Triphenylacetic Acid

Carboxylic acids are exhaustively C-methylated to t-butyl compounds by excess trimethylaluminium at c. 120�. Benzoic acid for example, gives t-butylbenzene. Similarly methylated are o-fluoro-, o-bromo-, and m-chloro-benzoic acids, 5-chloro-3-phenylsalicylic acid, 1-naphthoic acid, palmitic, oleic and undec-10-enoic acids. Adamantane-1-carboxylic acid gives mostly l-isopropenyladaman- tane, along with some 1-t-butyladamantane. Cinnamic acid gives mainly the allylically rearranged 2-methyl-4-phenylpent-2-ene. Triphenylacetic acid behaves atypically; 1,1,1-triphenylpropan-2-one and 3,3,3-triphenylpropyne result.

THE SYNTHESIS OF POSSIBLE DEGRADATION PRODUCTS OF METATHEBAINONE. I.

1944 ◽  
Vol 22b (3) ◽  
pp. 56-65 ◽  
Author(s):  
H. L. Holmes ◽  
L. W. Trevoy
Keyword(s):  
Carboxylic Acid ◽  
Ethyl Ester ◽  
Degradation Products ◽  
Aldehyde Group ◽  
Carboxyl Group ◽  
Unsuccessful Attempt ◽  
Naphthoic Acid ◽  
Relationship Of ◽  
The Relationship ◽  
General Method

The method of Crowley and Robinson (5) for the synthesis of 6-methoxy-3,4-dihydro-2-naphthoic acid has been modified to provide an improved and general method for the synthesis of 3,4-dihydro-2-naphthoic acids. The 7-methoxy-3,4-dihydro-2-naphthoic acid and its ethyl ester have been shown to react with butadiene and 2,3-dimethylbutadiene to give 3-methoxy-5,8,9,10,13,14-hexahydrophenanthrene-14-carboxylic acid and its 6,7-dimethyl derivative. The relationship of these hydrophenanthrenes to possible degradation products of morphine and metathebainone has been discussed. An unsuccessful attempt was made to lengthen the C14-chain by converting the carboxyl group to an aldehyde group by the Rosenmund method followed by condensation with malonic acid. The projected conversion failed in the first stage.

125. 1 : 9-Benzanthrone-8-carboxylic acid and dibenzanthronedicarboxylic acid from 8-bromo-1-naphthoic acid

1935 ◽  
pp. 571 ◽  
Author(s):  
H. Gordon Rule ◽  
William Pursell ◽  
A. John G. Barnett
Keyword(s):  
Carboxylic Acid ◽  
Naphthoic Acid

A Pyrolytic Approach to 2-Hydroxy-7-methoxy-5-methyl-1-naphthoic Acid

1995 ◽  
Vol 48 (5) ◽  
pp. 1055 ◽  
Author(s):  
RFC Brown ◽  
FW Eastwood ◽  
JM Horvath
Keyword(s):  
Carboxylic Acid ◽  
Condensation Product ◽  
Quantitative Yield ◽  
Meldrum's Acid ◽  
Meldrum’S Acid ◽  
Title 1 ◽  
Flash Vacuum Pyrolysis ◽  
Vacuum Pyrolysis ◽  
Naphthoic Acid

Condensation of 4-methoxy-2,6-dimethylbenzaldehyde with Meldrum's acid, and flash vacuum pyrolysis of the condensation product (12) gave in almost quantitative yield 7-methoxy-5-methyl-2-naphthol (9). This naphthol is a precursor of the title 1-carboxylic acid (6), an intercalating moiety of enediyne and other antibiotics.

Wholly aromatic polyesters derived from 6-hydroxy-5-phenyl-2-naphthoic acid and 4'-hydroxy-3′ -phenylbiphenyl-4-carboxylic acid

1995 ◽  
Vol 96 (1) ◽  
pp. 125-134 ◽  
Author(s):  
Jung-Il Jin ◽  
Seung-Moo Huh
Keyword(s):  
Carboxylic Acid ◽  
Naphthoic Acid ◽  
Aromatic Polyesters

scholarly journals Crystal structure of 8-[7,8-bis(4-chlorobenzoyl)-7H-cyclopenta[a]acenaphthylen-9-yl]naphthalene-1-carboxylic acid

2015 ◽  
Vol 71 (1) ◽  
pp. 38-41
Author(s):  
Jomon P. Jacob ◽  
M. Sithambaresan ◽  
Christy Kunjachan ◽  
M. R. Prathapachandra Kurup
Keyword(s):  
Carboxylic Acid ◽  
Three Dimensional ◽  
Ring System ◽  
Domino Reaction ◽  
Central Ring ◽  
Compound C ◽  
Naphthoic Acid ◽  
Fused Ring ◽  
Π Stacking Interaction ◽  
Fused Ring System

The title compound, C40H22Cl2O4, was formed by a Michael–Aldol domino reaction sequence, which coupled acenaphthenequinone with 4-chloroacetophenone in the presence of KOH in methanol. The dihedral angles between the central cyclopenta[a]acenaphthylene fused-ring system (r.m.s. deviation = 0.066 Å) and the 4-chlorobenzoyl rings are 62.25 (10) and 70.19 (10)°. The dihedral angle between the central ring system and the naphthoic acid grouping is 62.46 (7)°. This twisting of the pendant rings facilitates the formation of an intramolecular aromatic π–π stacking interaction between the 4-chlorobenzoyl and naphthoic acid rings, with centroid–centroid distances of 3.4533 (16) and 3.5311 (16) Å, and a C—H...π interaction between one of the H atoms of the central moiety and the 4-chlorobenzoyl ring with an H...π distance of 2.57 Å. In the crystal, carboxylic acid inversion dimers generateR22(8) loops. The dimers are linked by weak C—H...O and C—H...Cl hydrogen bonds and C—H...π interactions, generating a three-dimensional architecture.

scholarly journals Oxidative Cleavage ofβ-Keto Sulfones via Nitrous Acid

2014 ◽  
Vol 2014 ◽  
pp. 1-4 ◽  
Author(s):  
Hatem A. Abdel-Aziz
Keyword(s):  
Carboxylic Acid ◽  
Formic Acid ◽  
Nitrous Acid ◽  
Oxidative Cleavage ◽  
Ring Cleavage ◽  
Cleavage Reaction ◽  
Chlorobenzoic Acid ◽  
Mechanistic Pathway ◽  
Naphthoic Acid

The reaction of nitrous acid with 1-aryl-2-(arylsulfonyl)ethanones3a–eafforded the unexpected arenecarboxylic acids12a–e, formic acid14, and benzene/4-toluenesulfinic acid15a,bthrough oxidative cleavage reaction. 4-Chlorobenzoic acid (12a), [1,1′-biphenyl]-4-carboxylic acid (12b), 2-naphthoic acid (12c), 2-thiophenecarboxylic acid (12d), and 2-benzofurancarboxylic acid (12e) were isolated in 72%, 62%, 55%, 58%, and 62% yields, respectively. The reported mechanistic pathways proposed the production of 1-aryl-2-(phenyl/tolylsulfonyl)ethane-1,2-dione7instead of arenecarboxylic acids12. A mechanistic pathway to explain the reaction of nitrous acid with 1-aryl-2-(arylsulfonyl)ethanones3a–ewas suggested. In this pathway, the intermediate 1,2-oxazete10lost benzene/4-toluenesulfinic acid15to produce 1,2-oxazet-3-one11. Ring cleavage of the latter intermediate afforded the arenecarboxylic acids12.

scholarly journals STUDIES IN THE CYCLIZATION OF THE PRODUCTS OF STOBBE CONDENSATION WITH PROPIOPHENONE

1965 ◽  
Vol 43 (8) ◽  
pp. 2408-2414 ◽  
Author(s):  
A. M. El-Abbady ◽  
S. H. Doss
Keyword(s):  
Carboxylic Acid ◽  
Acetic Anhydride ◽  
Sodium Acetate ◽  
Catalytic Reduction ◽  
Stannic Chloride ◽  
Unsaturated Ester ◽  
Isomeric Mixture ◽  
Keto Ester ◽  
Diethyl Succinate ◽  
Naphthoic Acid

The isomeric mixture of the half-esters resulting from the Stobbe condensation of propiophenone with diethyl succinate is cyclized with stannic chloride as well as with sodium acetate in acetic anhydride. Cyclization of the ethyl half-ester chlorides with stannic chloride gives the keto-ester "4-carbethoxy-2-methyl-3-phenylcyclopent-2-enone." This on acid hydrolysis and decarboxylation yields 2-methyl-3-phenylcyclopent-2-enone, from which 2-methyl-3-phenylcyclopentanone is prepared by catalytic reduction. The keto-ester on Clemmensen reduction gives the corresponding unsaturated ester from which 3-methyl-2-phenylcyclopentane-1-carboxylic acid is obtained by catalytic hydrogenation and hydrolysis. 2-Methyl-3-phenylcyclopentanone and 3-methyl-2-phenylcyclopentane-1-carboxylic acid are of interest as intermediates for analogues of steroid hormones. From the latter 3-methyl-2-phenylcyclopentyl hydroxymethyl ketone and its acetate are prepared.Cyclization of the isomeric mixture of the ethyl half-esters with sodium acetate in acetic anhydride gives methyl 4-acetoxy-1-ethyl-2-naphthoate which is converted into 1-ethyl-4-methoxy-2-naphthoic acid.

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