Study of the Reformatsky Reaction; Efficient Procedure for the Preparation of Bromoacetic Ester in Large Quantities

Natelson, Samuel; Gottfried, Sidney P.

doi:10.1021/ja01873a508

Cited by 23 publications

(6 citation statements)

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“…(1-Hydroxycyclohexan-1yl)acetic acid was routinely prepared by the method of Watanabe et al (30), using lithium-naphthalene to synthesize the compound from cyclohexanone and acetic acid. (1-Hydroxycyclopentan-1-yl)acetic acid, (1-hydroxycycloheptan-1-yl)acetic acid, and, occasionally, (1-hydroxycyclohexan-1-yl)acetic acid were prepared by the Reformatsky reaction as described by Natelson and Gottfried (18). Cyclohexylideneacetic acid was prepared from (1-hydroxycyclohexan-1-yl)acetic acid by dehydration with acetic anhydride according to the procedure of Beesley et al…”

Section: Growth Ofmentioning

confidence: 99%

Metabolism of cyclohexaneacetic acid and cyclohexanebutyric acid by Arthrobacter sp. strain CA1

Ougham¹,

Trudgill²

1982

J Bacteriol

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A strain of Arthrobacter was isolated by enrichment culture with cyclohexaneacetate as the sole source of carbon and grew with a doubling time of 4.2 h. In addition to growing with cyclohexaneacetate, the organism also grew with cyclohexanebutyrate at concentrations not above 0.05%, and with a variety of alicyclic ketones and alcohols. Oxidation of cyclohexaneacetate proceeded through formation of the coenzyme A (CoA) ester followed by initiation of a (oxidation cycle. 3-Oxidation was blocked before the second dehydrogenation step due to the formation of a tertiary alcohol, and the side chain was eliminated as acetyl-CoA by the action of (1-hydroxycyclohexan-1-yl)acetyl-CoA lyase. The cyclohexanone thus formed was degraded by a well-described route that involves ring-oxygen insertion by a biological Baeyer-Villiger oxygenase. All enzymes of the proposed metabolic sequence were demonstrated in cell-free extracts. Arthrobacter sp. strain CAl synthesized constitutive (-oxidative enzymes, but further induction of enzymes active toward cyclohexaneacetate and its metabolites could occur during growth with the alicyclic acid. Other enzymes of the sequence, (1hydroxycyclohexan-1-yl)acetyl-CoA lyase and enzymes of cyclohexanone oxidation, were present at neglWble levels in succinate-grown cells but induced by growth with cyclohexaneacetate. The oxidation of cyclohexanebutyrate was integrated into the pathway for cyclohexaneacetate oxidation by a single (oxidation cycle. Oxidation of the compound could be divided into two phases. Initial oxidation to (1-hydroxycyclohexan-1-yl)acetate could be catalyzed by constitutive enzymes, whereas the further degradation of (1-hydroxycyclohexan-1-yl)acetate was dependent on induced enzyme synthesis which could be inhibited by chloramphenicol with the consequent accumulation of cyclohexaneacetate and (1-hydroxycyclohexan-1-yl)acetate.

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Section: Growth Ofmentioning

confidence: 99%

Metabolism of cyclohexaneacetic acid and cyclohexanebutyric acid by Arthrobacter sp. strain CA1

Ougham¹,

Trudgill²

1982

J Bacteriol

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“…1,3-Diols were prepared by the following methods, (1) alkylation of ethyl acetoacetate,") acetylacetone, 6) and diethyl malonate 7l with alkyl halides, followed by reduction with LiAlH 4 ; (2) direct ethoxycarbonylation of ethyl phenyl acetate, 8) followed by reduction with LiAlH 4 ; (3) condensation of diethyl malonate with acetone, followed by treating with Grignard reagents in the presence of CuCl,9) and then reduction; (4) preparation of 3-hydroxyesters from aldehydes and ethyl bromoacetate 10 ) by the Reformatsky reaction, followed by reduction.…”

Section: Syntheses Of 1 3-diolsmentioning

confidence: 99%

Synthesis of 1,3-Dithiane-2-thiones

Kubota¹,

Taniguchi²,

Etō³

et al. 1977

Agricultural and Biological Chemistry

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“…2-Phenyl-3,4-dihydro-l-phenanthreneacetic acid, IVa. In the best of several experiments, 13 g. of sandpapered zinc foil (16) was added to a hot solution of 36.8 g. of ketone, Ilia, and 33.4 g. of ethyl bromoacetate in 350 cc. of toluene and 150 cc.…”

Section: -Methylpicene Synthesismentioning

confidence: 99%