Borane → (4-Phenoxyphenyl)methanol

HRID 1781142Notes

Reaction equation

HRID 1781142 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.[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C>[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

6

Reactant 3

HCID 6331BoraneHCID 25517Ammonium ChlorideHCID 661394-Phenoxybenzaldehyde

Product 1

HCID 826195(4-Phenoxyphenyl)methanolYield 92%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. solution of 4-phenoxybenzaldehyde (5.0 g, 25.2 mmol) in 10 mL THF under an atmosphere of dry N2 was treated with borane (1.0M in THF, 11.25 mL) for 1 hour. A saturated NH4Cl solution was added, and the mixture was diluted with ethyl acetate. The organic layer was washed with 1M HCl, 5% NaHCO3 and brine, dried and concentrated in vacuo to give the title compound in 92% yield.

Workup

  1. washThe organic layer was washed with 1M HCl, 5% NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da791c1d03e640cea0191e88eb7cbea9
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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