Bromination of Tetralin. Short and Efficient Synthesis of 1,4-Dibromonaphthalene

2000 ◽  
Vol 65 (11) ◽  
pp. 1791-1804 ◽  
Author(s):  
Osman Çakmak ◽  
Ismail Kahveci ◽  
Íbrahim Demirtaş ◽  
Tuncer Hökelek ◽  
Keith Smith
Keyword(s):  
High Temperature ◽  
Major Product ◽  
High Yield ◽  
Efficient Synthesis ◽  
Secondary Products ◽  
Derivatives Of ◽  
Sole Product

High-temperature bromination of tetralin (1,2,3,4-tetrahydronaphthalene) with bromine resulted in benzylic bromination to give 1,4-dibromo-1,2,3,4-tetrahydronaphthalene (4) as a major product and several secondary products. Photolytic bromination of tetralin and subsequent double dehydrobromination of 1,1,4,4-tetrabromo-1,2,3,4-tetrahydronaphthalene (10) gave 1,4-dibromonaphthalene (11) as the sole product in a high yield. 1,4-Dibromonaphthalene is efficiently converted to the corresponding methoxy (12 and 13) and cyano (14 and 15) derivatives of naphthalene.

O-Isopropylidene derivatives of D-allulose (D-psicose) and D-erythro-hexopyranos-2,3-diulose

1968 ◽  
Vol 46 (8) ◽  
pp. 765-770 ◽  
Author(s):  
G. M. Cree ◽  
A. S. Perlin
Keyword(s):  
Deuterium Oxide ◽  
Spectral Characteristics ◽  
High Yield ◽  
Partial Acid Hydrolysis ◽  
Hydride Reduction ◽  
Sodium Amalgam ◽  
Isopropylidene Derivatives ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
Sole Product

Oxidation of 1,2: 4,5-di-O-isopropylidene-β-D-fructopyranose (2) with ruthenium tetroxide affords crystalline 1,2: 4,5-di-O-isopropylidene-β-D-erythro-hexopyranos-2,3-diulose (3) in high yield. The latter, on reduction with metal hydrides or on catalytic hydrogenation over platinum, yields 1,2: 4,5-di-O-isopropylidene-β-D-allulopyranose (4) as virtually the sole product. By contrast, sodium amalgam reduction of 3 yields only the D-fructose derivative (2), although in low yield. Also, metal hydride reduction of impure 3, obtained by oxidation of 2 with dimethyl sulfoxide – acetic anhydride, yields equal amounts of both isomers (2 and 4). The stereochemistry of these reductions is complicated by uncertainty as to the conformation of 4 (and possibly of 2), owing to anomalous proton magnetic resonance spectral characteristics observed.Ketone 3, which is unstable in the presence of deuteroxide ion, is smoothly deuterated at C-4 by exchange in hot deuterium oxide – pyridine.Mono-O-isopropylidene derivatives have been prepared by partial acid hydrolysis of 2 and 4.

scholarly journals An Efficient Synthesis of Milnacipran Hydrochloride via Reductive Amination of Aldehyde

2017 ◽  
Vol 2017 ◽  
pp. 1-6
Author(s):  
Neha Reddy Desireddy ◽  
Arava Glory ◽  
Krishna Reddy Bhimireddy ◽  
Yadagiri Kurra ◽  
Ram Reddy
Keyword(s):  
Primary Amine ◽  
Reductive Amination ◽  
Major Product ◽  
Important Application ◽  
Water Soluble ◽  
High Yield ◽  
Efficient Synthesis ◽  
By Products

An efficient synthesis of milnacipran hydrochloride has been accomplished. The important application of this paper is the reductive amination of aldehyde to primary amine with water soluble reagents. This method provides a high yield of primary amine as the major product, reduces the number of steps, and discourages by-products.

scholarly journals Multistep batch-flow hybrid synthesis of a terbinafine precursor

2021 ◽  
Author(s):  
Tamás Hergert ◽  
Béla Mátravölgyi ◽  
Róbert Örkényi ◽  
János Éles ◽  
Ferenc Faigl
Keyword(s):  
Methyl Ether ◽  
Lithium Salt ◽  
Scale Up ◽  
Hybrid Process ◽  
High Yield ◽  
Grignard Reaction ◽  
Efficient Synthesis ◽  
Synthetic Process ◽  
Synthesis Route ◽  
Selective Addition

AbstractA three-step batch-flow hybrid process has been developed for an expeditious synthesis of the enynol key intermediate of antifungal terbinafine. This procedure involves consecutive organometallic steps without the necessity of any in-line purification: after a metalation by n-butyllithium, a selective addition of the lithium salt was elaborated followed by a Grignard reaction resulting in a high yield of 6,6-dimethylhept-1-en-4-yn-3-ol. Moreover, as an alternative to tetrahydrofuran, cyclopentyl methyl ether was used as solvent implementing a safe, sustainable, yet selective synthetic process. Even on a laboratory-scale, the optimized batch-flow hybrid process had a theoretical throughput of 41 g/h. Furthermore, the newly developed process provides an efficient synthesis route to the key-intermediate, while making acrolein obsolete, minimizing side-products, and enabling safe and convenient scale-up.

Preparation and Pyrolysis of Stereoisomeric Bromobicyclo[n.1.0]alkanes ( n = 6, 8 , 10)

1987 ◽  
Vol 42 (4) ◽  
pp. 489-494 ◽  
Author(s):  
Eckehard V. Dehmlow ◽  
Roland Kramer
Keyword(s):  
Thermal Stability ◽  
Gas Phase ◽  
Condensed Phase ◽  
Secondary Products ◽  
Gas Phase Reactions ◽  
Stereoselective Reduction ◽  
Derivatives Of ◽  
Thermal Stability Of

Abstract The title compounds la-3c were prepared by stereoselective reduction of the respective dibromides. Pyrolysis gave allylic bromides (8, 9, 11) as primary and dienes (10, 12) as secondary products. Product ratios were independent of the stereochemistry of the starting materials. No differences of the rearrangement rates of the stereoisomers were observed in gas phase reactions of the derivatives of bicyclo[6.1.0]- and bicyclo[8.1.0]alkanes. With the larger bicyclo[10.1.0] derivatives, however, distinct differences in the thermal stability of cis-trans-isomers4c/5c or 2c/3c were found in condensed phase.

Enantioselective synthesis of (R)-tolterodine using lithiation/borylation–protodeboronation methodology

2012 ◽  
Vol 90 (11) ◽  
pp. 965-974 ◽  
Author(s):  
Stefan Roesner ◽  
Varinder K. Aggarwal
Keyword(s):  
Enantioselective Synthesis ◽  
High Yield ◽  
Magnesium Bromide ◽  
Efficient Synthesis ◽  
Boronic Ester ◽  
Better Than

The synthesis of the pharmaceutical (R)-tolterodine is reported using lithiation/borylation–protodeboronation of a homoallyl carbamate as the key step. This step was tested with two permutations: an electron-neutral aryl Li-carbamate reacting with an electron-rich boronic ester and an electron-rich aryl Li-carbamate reacting with an electron-neutral boronic ester. It was found that the latter arrangement was considerably better than the former. Further improvements were achieved using magnesium bromide in methanol leading to a process that gave high yield and high enantioselectivity in the lithiation/borylation reaction. The key step was used in an efficient synthesis of (R)-tolterodine in a total of eight steps in a 30% overall yield and 90% ee.

scholarly journals Effect of hydrothermal pretreatment of corn stover with pH adjustment on properties of pulp and hydrolysate

BioResources ◽  
2020 ◽  
Vol 15 (3) ◽  
pp. 6826-6839
Author(s):  
Junjun Kong ◽  
Ling Zhang ◽  
Ziyi Niu ◽  
Rina Wu ◽  
Gaosheng Wang
Keyword(s):  
Sodium Hydroxide ◽  
Corn Stover ◽  
Ph Value ◽  
Major Product ◽  
Hydrothermal Pretreatment ◽  
Raw Material ◽  
High Yield ◽  
Pulp Yield ◽  
Industrial Utilization ◽  
The Relationship

In view of environmental and economic issues, co-production technology with pulp as the major product is an important developmental direction in biorefinery. In this paper, high-yield pulp was prepared by hydrothermal pretreatment with controlled pH and subsequent mechanical refining using corn stover as raw material. By adding acetic acid or sodium hydroxide, the properties of the hydrolysate and the pulp were altered. Reducing the pH during hydrothermal pretreatment resulted in more cellulose and hemicellulose being released, while less lignin was released. Increased pH led to more lignin being released, while dissolution of carbohydrates did not change significantly. A maximum pulp yield at pH 5.84 of hydrolysate was obtained when 3.0% sodium hydroxide was used. The strength of pulp is highly related to the removal of lignin during hydrothermal pretreatment. The relationship between pH value in hydrothermal pretreatment and the physical properties of the pulp was established and could be further used for prediction and as guidance for process control. Moreover, the results could be used to develop technologies for industrial utilization of agricultural straw to co-generate fiber and other bio-based products.

One-step catalytic amination of naphthalene to naphthylamine with exceptional yield

2020 ◽  
Vol 22 (9) ◽  
pp. 2744-2749
Author(s):  
Fang Hao ◽  
Xin Wang ◽  
Linfang Huang ◽  
Wei Xiong ◽  
Pingle Liu ◽  
...  
Keyword(s):  
Mild Condition ◽  
Major Product ◽  
High Yield ◽  
Vanadium Catalysts ◽  
Catalytic Amination ◽  
One Step ◽  
First Time

This is the first time to synthesize naphthylamine from one-step naphthalene amination by vanadium catalysts with high yield under mild condition. It could obtain ∼70% yield of naphthylamine, with major product of valuable 1,5-diaminonaphthalene.

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