Synthesis of Bromoacetals

Bedoukian, Paul Z.

doi:10.1021/ja01232a501

Cited by 32 publications

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“…α-Bromoaldehydes are important organic intermediates in pharmaceutical and fine chemical industries with a significant industrial value. These are usually synthesized − by direct bromination of aldehydes or by bromination of the dimethylacetal of the aldehyde followed by hydrolysis. In both cases bromination is usually done by liquid bromine.…”

Section: Introductionmentioning

confidence: 99%

Studies in Selectivity Aspects in the Synthesis of Aliphatic α-Bromoaldehydes

Mukhopadhyay

1999

Org. Process Res. Dev.

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A highly selective process scheme was developed to synthesize r-bromoaldehydes by regulating the important process parameters from a reaction-engineering point of view. Thus, r-bromobutyraldehyde and r-bromoheptaldehyde were synthesized in very high selectivity starting with butyraldehyde and heptaldehyde. In the bromination reaction at 40% conversion ratio, the selectivity was as high as 98% by using liquid bromine as the brominating agent.

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Section: Introductionmentioning

confidence: 99%

Studies in Selectivity Aspects in the Synthesis of Aliphatic α-Bromoaldehydes

Mukhopadhyay

1999

Org. Process Res. Dev.

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“…The acid chlorides of indole-2-carboxylic acid, 5-cyanoindole-2-carboxylic acid (X), and 5-carbethoxyaminoindole-2-carboxylic acid (XXI) are converted to indole-2-carboxyacetalylbenzylamide derivatives by reaction with benzylaminoacetal. The latter is synthesized with slight modification by the method of Rugheimer and Schon (11) from benzylamine and bromoacetal (12). The resulting N-benzylamides, XXII, XXVI, and XXIV, are cyclized with ethereal sulfuric acid and the products purified by fractional recrystallization from dioxane solution.…”

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confidence: 99%

“…Bromoacetal. Bromoacetal was obtained in 76% yield from vinyl acetate, bromine, and absolute alcohol, following the method described by Bedoukian (12). Benzylaminoacetal.…”

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confidence: 99%

Synthesis and Reactions of Indole Carboxylic Acids; Pyridindolones From Indole-2-Carboxyacetalylbenzylamides

Lindwall¹,

Mantell²

1953

J. Org. Chem.

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This study is a continuation of the work in this laboratory on the preparative methods and chemistry of indole derivatives. Of particular interest are those indole carboxylic acids containing the carboxylic acid group in the five position arid having an unsubstituted three position. These compounds resemble anesthesiiie in structure and may be converted to warped amino acids by the Maniii ch reaction.An outgrowth of this work is the preparation arid ring closure of a few indole-2-carboxybenzylacetalylamides to determine the orienting effects of groups substituted in the five position. R = COOH I R = C'OOH 111 R = C0OI-I R = CO?C?H, I1 R = C02C2Hj R = C S 1-1 R = C S

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Diethyl Mercaptoacetal

Parham

Wynberg

2003

Organic Syntheses

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Diethyl mercaptoacetal reactant: 588 g. (3 moles) of diethyl bromoacetal intermediate: 500 g. (1.38 moles, calculated as tetrasulfide) of 1,1,1′,1′‐tetraethoxyethyl polysulfide byproduct: 1,1,1′,1′‐tetraethoxyethyl sulfide product: Diethyl mercaptoacetal

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Synthesis of Bromoacetals

Abstract: The products obtained by the dehydration and the acetylative dehydration of hydantoin-5-propionic acid have been shown to possess the lactam structure IV and V. Chagrin Falls, Ohio

Cited by 32 publications

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Studies in Selectivity Aspects in the Synthesis of Aliphatic α-Bromoaldehydes

Studies in Selectivity Aspects in the Synthesis of Aliphatic α-Bromoaldehydes

Synthesis and Reactions of Indole Carboxylic Acids; Pyridindolones From Indole-2-Carboxyacetalylbenzylamides

Diethyl Mercaptoacetal

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