ChemicalBook CAS DataBase List (S)-(+)-HEXAHYDROMANDELIC ACID

(S)-(+)-HEXAHYDROMANDELIC ACID synthesis

7synthesis methods

Product Name:(S)-(+)-HEXAHYDROMANDELIC ACID
CAS Number:61475-31-8
Molecular formula:C8H14O3
Molecular Weight:158.2

17199-29-0
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$5.00/10g

61475-31-8
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$170.00/1g

Yield:61475-31-8 90%

Reaction Conditions:

in methanol;cyclohexane;acetic acid;

Steps:

I.A A.

A. (S)(+)-Hexahydromandelic Acid (S)(+)-Mandelic acid (76.0 g) was dissolved in 440 ml methanol containing 5 ml glacial acetic acid. The phenyl ring was entirely reduced in the presence of 5 gm. of 5% rhodium-on-alumina catalyst under 100 psi H₂ pressure in 10 hrs. Following filtration of the solution through Celite (diatomaceous earth) to remove the catalyst, the methanol was removed via a rotary evaporator. The resulting white solid was dissolved in 1 liter (l) of hot diethyl ether and filtered while hot. The volume of the solution was reduced to 400 ml and 250 ml cyclohexane was added. The ether was then removed and the resultant cyclohexane solution was stored several hours under refrigeration. White crystals of the desired product formed and were collected via filtration. The solid was dried overnight in vacuo at 40° C. Seventy-one grams of (S)(+)-hexahydromandelic acid were obtained for a 90% yield: m.p. 128°-129° C. (lit., 129° C.) and [α]_D²³ =+23.5° (1, HOAc) (lit. [α]_D²³ =+25.5 (1.1, HOAc) for the (R) (+) isomer.

References:

US4331818,1982,A