Hydrochloric Acid → 1-Phenylethanol, (S)-

HRID 1265416Notes

Reaction equation

HRID 1265416 reaction equation
[OH-].[K+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].Cl>CC(O)C>[C:6]1([C@@H:3]([OH:5])[CH3:4])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7410AcetophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 4431351-Phenylethanol, (S)-Yield 84%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

The catalyst solution was added to a degassed 0.1M solution of KOH in 2-propanol, followed by a solution of acetophenone in 2-propanol. The mixture was stirred at ambient temperature under nitrogen for 2 h, then worked up by neutralising with dilute hydrochloric acid and concentrating by vacuum distillation. The residue was diluted with ethyl acetate and washed with an equal volume of saturated aqueous sodium chloride. The organic layer was separated, dried over magnesium sulphate, separated from the solid and freed of solvent to give crude (S)-1-phenylethanol (1.76 g). Yield 84%, ee 89%. The turnover number, integrated over 1 h, was 324 h−1.

Workup

  1. concentrationconcentrating by vacuum distillation
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with an equal volume of saturated aqueous sodium chloride
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. customseparated from the solid and freed of solvent

Sources & evidence

ORD record
ord-83a91cfcedf94879b40f2b684575dc7e
Source dataset
uspto-grants-2003_04
Patent number
US06545188B2

Reaction notes

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