Water → 2-Phenoxybenzyl alcohol

HRID 413506Notes

Reaction equation

HRID 413506 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>C1COCC1>[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

4

Reactant 2

HCID 962WaterHCID 752372-Phenoxybenzoic acid

Product 1

HCID 36601112-Phenoxybenzyl alcoholYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 1 M solution of borane-tetrahydrofuran complex (30 ml) was added dropwise to a stirred solution of 2-phenoxybenzoic acid (5.35 g) in dry THF (50 ml), cooled to 0° C. (effervescence). Following the addition, the mixture was stirred at 0° C. for 15 minutes, then at room temperature for 1.5 hours. It was poured into water and extracted with ether. The extracts were washed successively with water, aqueous sodium bicarbonate, aqueous sodium carbonate, then dried and concentrated under reduced pressure to give 2-phenoxybenzyl alcohol (4.83 g, 97%) as a colourless oil.

Workup

  1. additionthe addition
  2. waitat room temperature for 1.5 hours
  3. extractionextracted with ether
  4. washThe extracts were washed successively with water, aqueous sodium bicarbonate, aqueous sodium carbonate
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca431a18d3484495bb0c339fd296331b
Source dataset
uspto-grants-2003_05
Patent number
US06566547B1

Reaction notes

Loading…