Water → 2-Phenoxybenzyl alcohol

HRID 384121Notes

Reaction equation

HRID 384121 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>O1CCCC1.B.O1CCCC1>[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[CH2:10][OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 752372-Phenoxybenzoic acid

Product 1

HCID 36601112-Phenoxybenzyl alcohol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2723981Borane;tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-phenoxybenzoic acid (20.8 g) in tetrahydrofuran (400 ml), 14.6 ml of borane-tetrahydrofuran complex (1M tetrahydrofuran solution) was added, and the reaction solution was stirred at 50° C. for 4 hours. The reaction solution was cooled, then water was added, and the mixture was extracted with chloroform. The combined organic layers were washed with 1N aqueous sodium hydroxide and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford the title compound as a colorless oil.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionthe mixture was extracted with chloroform
  3. washThe combined organic layers were washed with 1N aqueous sodium hydroxide
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3e88cfd6629b4691a039c93ed8842a5f
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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