Potassium Carbonate → 4-([1,1′-Biphenyl]-4-ylmethoxy)benzenepropanol

HRID 1782753Notes

Reaction equation

HRID 1782753 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22](O)[CH2:23][CH3:24])=[CH:18][CH:17]=1.C(=O)([O-])[O-:27].[K+].[K+]>C(#N)CCC>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=[CH:13][C:10]([CH2:11][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][OH:27])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 13055557Benzenemethanol, α-ethyl-4-hydroxy-

Product 1

HCID 575890364-([1,1′-Biphenyl]-4-ylmethoxy)benzenepropanol

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Procedure

12.8 g (41.4 mmol) of 4-phenylbenzyl bromide, 6.94 g (45.6 mmol) of 4-hydroxy-phenylpropanol and 6.87 g (49.7 mmol) of potassium carbonate are stirred in 50 ml of butyronitrile at 120° C. for 6 hours. Cooling to room temperature is followed by removal of the inorganic salts by filtration with suction and concentration in vacuo. The crude product is purified by chromatography on silica gel 60 (mobile phase gradient cyclohexane-->cyclohexane/ethyl acetate 60:40). 4.90 g (37% of theory) of product are obtained.

Workup

  1. customis followed by removal of the inorganic salts by filtration with suction and concentration in vacuo
  2. customThe crude product is purified by chromatography on silica gel 60 (mobile phase gradient cyclohexane-->cyclohexane/ethyl acetate 60:40)
  3. custom4.90 g (37% of theory) of product are obtained

Sources & evidence

ORD record
ord-93a6c17c3c44457788a844ec68ab49dd
Source dataset
uspto-grants-2009_03
Patent number
US07498460B2

Reaction notes

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