(S)-mandelic acid → (2s)-Cyclohexyl(hydroxy)acetic 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.

1. filtrationfiltration of the solution through Celite® (diatomaceous earth)
2. customto remove the catalyst
3. customthe methanol was removed via a rotary evaporator
4. dissolutionThe resulting white solid was dissolved in 1 liter (l) of hot diethyl ether
5. filtrationfiltered while hot
6. additionwas added
7. customThe ether was then removed
8. waitthe resultant cyclohexane solution was stored several hours under refrigeration

ORDレコード

ord-88501b4e8d4f465897ddcf677eca2d8d

出典データセット

uspto-grants-1984_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04440936