Water → Benzenemethanol, 3-(2-phenylethyl)-

HRID 2254402Notes

Reaction equation

HRID 2254402 reaction equation
[CH2:1]([C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12](OCC)=[O:13])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[CH2:12][OH:13])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 19744689HCID 19744689, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10488743Benzenemethanol, 3-(2-phenylethyl)-Yield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-phenethylbenzoate (180 mg) was dissolved in 2 ml of anhydrous tetrahydrofuran, and under ice cooling, 42 mg of lithium aluminum hydride was added by portions over 5 minutes. The mixture was stirred for one hour under ice cooling. Water (10 ml) was added to the reaction mixture to decompose the excess of the reducing agent. The mixture was then extracted with 20 ml of ethyl ether. The extract was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated to give 140 mg (yield 93%) of 3-phenethylbenzyl alcohol.

Workup

  1. extractionThe mixture was then extracted with 20 ml of ethyl ether
  2. customThe extract was separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-80338d783f624d458692a0c1a526b432
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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