Stearyl Alcohol → 1-Phenylethanol, (R)-

HRID 1939755Notes

Reaction equation

C(O)CCCCCCCCCCCCCCCCC.[C:20]1([C@@H:26]([OH:28])[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:20]1([C@H:26]([OH:28])[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 2

HCID 8221Stearyl Alcohol

HCID 4431351-Phenylethanol, (S)-

Product 1

HCID 6375161-Phenylethanol, (R)-Yield 96%

Conditions

Temperature: 90 °C

Procedure

To the distillation residue were added 270 g of stearyl alcohol and 10 g of Lipase PL. The mixture was subjected to ultrasonication in the same manner as described above to regulate the particle size of the lipase in such a manner that 95% or more of the particles had a particle size of 20 to 50 μm. The water content of the reaction system was 0.04% by weight. The mixture was stirred at 90° C. and 350 rpm under reduced pressure of 3 mmHg for 12 hours to carry out interesterification while recovering the distillate to obtain highly pure (R)-(+)-1-phenylethanol (yield: 96%; chemical purity: 100%; optical purity: 100% ee).

Workup

customThe mixture was subjected to ultrasonication in the same manner
distillationinteresterification while recovering the distillate

Sources & evidence

ORD record: ord-60b3c96c30e04baeaf593696c2599fa1
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05696299

Reaction notes

Loading…