4-Hydroxybenzyl Alcohol → (4-Phenoxyphenyl)methanol

HRID 1678588Notes

Reaction equation

HRID 1678588 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].N1C2C(=CC=CC=2O)C=CC=1>CN1CCN(C)C1=O>[O:8]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 11575Iodobenzene

Product 1

HCID 826195(4-Phenoxyphenyl)methanolYield 7.4%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

A solution of iodobenzene (2.0 g, 9.7 mmol), 4-hydroxybenzyl alcohol (1.0 g, 8.1 mmol), potassium carbonate (0.67 g, 4.8 mmol), copper chloride(I) (0.016 g, 0.16 mmol) and 8-quinolinol (0.023 g, 0.16 mmol) in 1,3-dimethyl-2-imidazolidinone (5 mL) was stirred at 170° C. for 20 hours. The reaction solution was filtered, extracted with ethyl acetate, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3) to give the title compound (0.12 g, yield 7%) as an oily matter.

Workup

  1. filtrationThe reaction solution was filtered
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=7:3)

Sources & evidence

ORD record
ord-a39a7f13f047413b9d99ba97426b858f
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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