Water → 1-(p-Prenylphenyl)ethanol

HRID 1413830Notes

Reaction equation

HRID 1413830 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1)[CH:2]=[C:3]([CH3:5])[CH3:4].[BH4-].[Na+].O>CO>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([OH:14])[CH3:13])=[CH:10][CH:11]=1)[CH:2]=[C:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 11217703p-Prenylacetophenone

Product 1

HCID 132172751-(p-Prenylphenyl)ethanolYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 20.0 g of p-prenylacetophenone in 200 ml of methanol, 1.5 g of sodium borohydride was added at 20° C. with stirring. After stirring for 4 hours, 300 ml of water was added, the resulting solution was extracted with ethyl ether. The extract was washed with water, dried, concentrated and distilled to give 18.5 g of 1-(p-prenylphenyl)-ethanol, b.p. 107-108 °C/0.30 mmHg.

Workup

  1. stirringAfter stirring for 4 hours
  2. extractionthe resulting solution was extracted with ethyl ether
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. distillationdistilled

Sources & evidence

ORD record
ord-4bc2ae96455940ebb9b703c423bd48f7
Source dataset
uspto-grants-1981_02
Patent number
US04251543

Reaction notes

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