Hydrochloric Acid → 1-Phenylethanol

HRID 1858408Notes

Reaction equation

HRID 1858408 reaction equation
CC(O)C.C1(C)C=CC=CC=1.CC(C[AlH]CC(C)C)C.[C:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[CH3:22].Cl>>[CH3:22][CH:21]([OH:23])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 3776IsopropanolHCID 7410AcetophenoneHCID 14487Diisobutylaluminum hydride

Product 1

HCID 74091-PhenylethanolYield 163.8%

Procedure

2-Propanol (1.53 ml, 20 mmol) was added to 9.9 ml (10 mmol) of a toluene solution of DIBAH (1.02 M) at room temperature and the mixture was stirred at room temperature for 1 hour. Thereto was added 0.601 g of acetophenone, and the resultant mixture was stirred at room temperature for 6 hours, followed by hydrolysis with 1 N hydrochloric acid with ice cooling. Extraction with ethyl acetate and concentration gave 1.001 g of α-phenethyl alcohol as an oil. Conversion 55%, yield 47.7%.

Workup

  1. extractionExtraction
  2. concentrationwith ethyl acetate and concentration

Sources & evidence

ORD record
ord-de774cd4c4ce4789959980b7f1c5dddf
Source dataset
uspto-grants-2000_11
Patent number
US06150567

Reaction notes

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