Cyclohexane → 1-(2-Bromophenyl)ethan-1-ol

HRID 1939752

Reaction equation

HRID 1939752 reaction equation
C1CCCCC1.C([O:30][CH:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[Br:39])[CH3:32])(=O)CCCCCCCCCCCCCCCCCCCCC>O>[Br:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[C@@H:31]([OH:30])[CH3:32]

Participants

4

Procedure

Interesterification was carried out by using 5 g of Lipase P of Pseudomonas fluorescens origin (a product of Amano Pharmaceutical Co., Ltd.), 10 g of (R,S)-1-2-(bromophenyl)ethanol, 30 g of tribehen and 450 ml of cyclohexane at 50° C. for 72 hours in the same manner as in Example 8. The water content of the reaction system was 0.01% by weight, and 90% of the lipase particles had a particle size of 30 to 50 μm. Gas chromatography of the reaction mixture revealed that 48 mol % of (R,S)-1-(2-bromophenyl)ethanol had been converted to 1-(2-bromophenyl)ethyl behenate. The reaction mixture was treated in the same manner as in Example 8, and the residue was subjected to simple distillation at 110° C. and 5 mmHg to recover unreacted (S)-(-)-1-(2-bromophenyl)ethanol (yield: 82%; chemical purity: 99.9%; optical purity: 98% ee).

Workup

  1. additionThe reaction mixture was treated in the same manner as in Example 8
  2. distillationthe residue was subjected to simple distillation at 110° C.

Sources & evidence

ORD record
ord-34c2dfe66184439aa444fd21605461f1
Source dataset
uspto-grants-1997_12
Patent number
US05696299

Linked notes

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