Water → 1-Phenylethanol, (S)-

HRID 1939743Notes

Reaction equation

HRID 1939743 reaction equation
CCCCCCCCCCCCCCCC(=O)OCC(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC.O.C([O:76][CH:77]([C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1)[CH3:78])(=O)CCCCCCCCCCCCCCC>CC(C)=O>[C:79]1([C@@H:77]([OH:76])[CH3:78])[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11147TripalmitinHCID 21468171HCID 21468171, compound

Product 1

HCID 4431351-Phenylethanol, (S)-Yield 87%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
85 °C

Procedure

In a 300 ml separable flask were put 3 g of Lipase PL of Alcaligenes sp. origin (a product of Meito Sangyo Co., Ltd., hereinafter the same applies) and 50 g of (R,S)-1-phenylethanol, and the mixture was subjected to ultrasonication with the same ultrasonic wave generating equipment as used in Example 1 at room temperature and at 20 kHz for 20 minutes. To the dispersion was added 150 g of tripalmitin, followed by stirring at 85° C. and 100 rpm for 30 hours to carry out interesterification. The water content of the reaction system was 0.05% by weight, and 93% of the lipase particles had a particle size of 15 to 40 μm. Gas chromatographic analysis of the reaction mixture revealed that 46 mol % of (R,S)-1-phenylethanol had been converted to 1-phenylethyl palmitate. To the reaction mixture was added 1500 ml of acetone, followed by cooling to 10° C. Lipase, unreacted tripalmitin, dipalmitin, monopalmitin, and palmitic acid were removed by filtration using Toyo Filter Paper No. 5A, and the filtrate was subjected to simple distillation at 95° C. under reduced pressure of 5 mmHg to give (S)-(-)-phenylethanol (yield: 87%; chemical purity: 99.9%; optical purity: 86.3% ee). The residue, i.e., (R)-(+)-1-phenylethanol palmitic acid ester was alkali-hydrolyzed in the same manner as in Example 1 to obtain (R)-(+)-1-phenylethanol (yield: 82%; chemical purity: 99.5%; optical purity: 98.0% ee).

Workup

  1. customIn a 300 ml separable flask were put
  2. customthe mixture was subjected to ultrasonication with the same ultrasonic wave
  3. wait100 rpm for 30 hours to carry out
  4. temperatureby cooling to 10° C
  5. customLipase, unreacted tripalmitin, dipalmitin, monopalmitin, and palmitic acid were removed by filtration
  6. filtrationFilter Paper No
  7. distillation5A, and the filtrate was subjected to simple distillation at 95° C. under reduced pressure of 5 mmHg

Sources & evidence

ORD record
ord-9133fc22082043c5bf5e65e6e51ac82c
Source dataset
uspto-grants-1997_12
Patent number
US05696299

Reaction notes

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