Water → 4-(3-(2-Benzyloxyphenyl)propyl]benzoic acid

HRID 2394998

Reaction equation

HRID 2394998 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O-:17])=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH2:26]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:18][CH:19]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 189738204-[3-(2-Hydroxyphenyl)propyl]benzoate

Product 1

HCID 189737644-(3-(2-Benzyloxyphenyl)propyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[3-(2-hydroxyphenyl)propyl]benzoate (1.0 g) in DMF (20 ml) was added potassium carbonate (0.76 g) and benzyl bromide (0.66 ml). The mixture was stirred for 18 hours, poured into water (100 ml) and ethyl acetate (100 ml). The ethyl acetate solution was washed with water (3×100 ml), dried (magnesium sulphate), filtered and evaporated. The residue was purified by subjecting to chromatography on silica gel using diethyl ether: hexane (1:9) as eluant. There was thus obtained methyl 4-[3-(2-benzyloxy-phenyl)propyl]benzoate (0.7 g) as an oil.

Workup

  1. washThe ethyl acetate solution was washed with water (3×100 ml)
  2. dry with materialdried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-e16c852fe2a1405bbb1ddb02dd1b6999
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Linked notes

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