Borane → (4-Phenoxyphenyl)methanol

HRID 1957336Notes

Reaction equation

HRID 1957336 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>O1CCCC1>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][OH:13])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 661394-Phenoxybenzaldehyde

Product 1

HCID 826195(4-Phenoxyphenyl)methanolYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-phenoxybenzaldehyde (5.0 g, 25 mmol) in dry tetrahydrofuran (10 mL) at 0° C. was treated with borane (1M in tetrahydrofuran, 11.25 mL). After 45 minutes, the reaction was quenched with saturated NH4Cl, diluted with ethyl acetate, and washed with 1M HCl, 5% NaHCO3, and brine, and dried over Na2SO4, and concentrated under reduced pressure to give 4.7 g (92%) of 4-phenoxybenzyl alcohol.

Workup

  1. customthe reaction was quenched with saturated NH4Cl
  2. additiondiluted with ethyl acetate
  3. washwashed with 1M HCl, 5% NaHCO3, and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-62b1e9d774f24ccdb57fe0138b3058c0
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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