Benzhydrol → 2-Chloro-1-phenylethanol, (+)-

HRID 635567Notes

Reaction equation

HRID 635567 reaction equation
CCCCCC.C([Al](CC(C)C)CC(C)C)C(C)C.C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=CC=1.C(O)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:56]([Cl:65])[C:57]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:58]>C1(C)C=CC=CC=1>[Cl:65][CH2:56][C@H:57]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)[OH:58]

Participants

7

Reactant 5

HCID 7037BenzhydrolHCID 8058HexaneHCID 107572-ChloroacetophenoneHCID 11762BinolHCID 16682931Triisobutylaluminum

Product 1

HCID 6433232-Chloro-1-phenylethanol, (+)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 0.5 ml (0.5 mmol) of hexane solution of triisobutylaluminum (1.0 M) was added a slurry solution of 143 mg (0.5 mmol) of (R)-1,1′-bi-2-naphthol in 10 ml of toluene at room temperature, and the mixture was stirred at room temperature for 30 minutes. Thereto 1.84 g (20 mmol) of benzhydrol was added and the mixture was stirred further at room temperature for 30 minutes. Thereto 1.55 g (10 mmol) of phenacyl chloride was added and the mixture was stirred further at room temperature for 2 hours. The after-treatment and the analysis of the product were then carried out in the same manner as described in Example 2.

Workup

  1. stirringthe mixture was stirred further at room temperature for 30 minutes
  2. stirringthe mixture was stirred further at room temperature for 2 hours

Sources & evidence

ORD record
ord-50eb9afafc71428b9b8c1823f7311769
Source dataset
uspto-grants-2001_02
Patent number
US06187966B1

Reaction notes

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