1 -hydroxycyclohexanecarboxylate

Acetylcyclohexanol has been prepared by the hydrolysis of 1-bromo-l-acetylcyclohexane3 and of 1-acetoxy-l-acetylcyclo-hexane oxime,7 by the hydration of 1-ethynylcyclohexanol,4 6 8 9 and by the treatment of 1-hydroxycyclohexanecarboxylic acid with methyllithium.10 The present procedure is based on that of Stacy and Mikulec for 1-acetylcyclopentanol.6... 

Hydroxy-cis-9-octadecenoic (ricinoleic) acid, physical properties, 5 35t 14-Hydroxy-cis-ll-eicosenoic (lesquerolic) acid, physical properties, 5 35t Hydroxycitronellal, 24 489, 490, 533—534 Hydroxy-containing organics, 20 794-795 3-Hydroxycyclohexanecarboxylic acid, 22 21... 

Reactions. w-Hydroxybenzoic acid affords a variety of products, depending on the catalyst and conditions employed. Catalytic reduction over platinum black or platinum oxide in alkaline solution gives 3-hydroxycyclohexanecarboxylic acid [22267-35-2]. Reduction of a warm aqueous solution over platinum oxide or over colloidal platinum yields cyclohexanecarboxylic acid. w-Hydroxybenzaldehyde can be prepared by reducing ///-hydroxybenzoic acid with sodium amalgam. Finally, reduction over Raney nickel gives cydohexanol. 

Sewell AC, Bohles HJ (1991) 4-Hydroxycyclohexanecarboxylic acid a rare compound in urinary organic acid analysis. Clin Chem 37 1301-1302... 

Although the most stable conformation of ds-3-hydroxycyclohexanecarboxylic acid has both substituents equatorial and is unable to close to a lactone, the diaxial orientation is accessible and is capable of lactone formation. 

Neither conformation of frans-3-hydroxycyclohexanecarboxylic acid has the substituents close enough to each other to form an unstrained lactone. 

The possibility that HCo(CO)4 is reacting by a concerted cis addition is ruled out at least in the case of cyclohexene oxide by the isolation of transmethyl 2-hydroxycyclohexanecarboxylate as the only product (54). This has recently been confirmed by Roos et al. (124), who obtained a dimer of trawr-hexahydrosalicylaldehyde. 

The reaction is rapid at first, but the catalyst is quickly exhausted. p-HydrOxybenzoic acid gives 4-hydroxycyclohexanecarboxylic acid (4Sf%) and cyclohexanecarboxylic acid (27%). Less success is achieved in the preparation of aminocyclohexanecatboxylic acids. Rates of hydrogenation of eleven phenyl-substituted aliphatic acids have been studied. With increased molecular complexity, higher pressures and larger amounts of catalyst are required. ... 

Problem 26.18 (a) Give structural formulas of compounds C-E. 4-hydroxycyclohexanecarboxylic acid + (CH3) C(NH2)CH20H —>... 

Inspection of molecular models of the different nonulosaminic acids indicates why these 4-hydroxy acids fail to form a 1,4-lactone. Sterically, they resemble m-hydroxycyclohexanecarboxylic acids, only the ds isomer of which yields a lactone (at 130°). 

Michael and aldol reaction tandem. Michael reaction products arising from dicarbonyl compounds that contain one conjugated double bond undergo cyclization (aldol reaction) if the second carbonyl group is properly juxtaposed. For example, a synthesis of 2-hydroxycyclohexanecarboxylic acid derivatives is accomplishable in one step from 7-keto-2-alkenamides. The tandem reaction is promoted by MejAlCl. 

Jranx-S-Hydroxycyclohexanecarboxylic acid lactone formation impossible... 

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