(R)-3-phenyllactic acid → (αR)-α-Hydroxycyclohexanepropanoic acid

HRID 962948Notes

Reaction equation

HRID 962948 reaction equation
[C:1]1([CH2:7][C@@H:8]([OH:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.[Pt](=O)=O>[CH:1]1([CH2:7][C@@H:8]([OH:12])[C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 643327(R)-3-phenyllactic acid2×

Product 1

HCID 54438349(αR)-α-Hydroxycyclohexanepropanoic acid

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

5 g (30.1 mmole) of 3-phenyl-D-lactic acid [Rf (2)=0.45-0.55] is dissolved in 70 ml of acetic acid and submitted to hydrogenation in the presence of 0.25 g of platinum(IV)oxide catalyst in the temperature range of 40° to 50° C. The reaction is monitored by thin-layer chromatography [final product: Rf (2)=0.6-0.7]. After completed reaction the catalyst is filtered off, the filtrate is evaporated from a water bath at a temperature not higher than 40° C., at 20-25 millibar. Then 20 ml of toluene is evaporated twice from the residue which is finally recrystallized from n-hexane.

Sources & evidence

ORD record
ord-76c82df6b5e24b31a4757eb82b6525a8
Source dataset
uspto-grants-1998_06
Patent number
US05760235

Reaction notes

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