4-[3-(2-Benzylphenyl)prop-1-enyl]benzoic acid → 4-[3-(2-Benzylphenyl)propyl]benzoic acid

HRID 1006041Notes

Reaction equation

HRID 1006041 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH:15]=[CH:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[Pd]>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][CH2:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 544026144-[3-(2-Benzylphenyl)prop-1-enyl]benzoic acid

Product 1

HCID 226755384-[3-(2-Benzylphenyl)propyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[3-(2-benzylphenyl)prop-1-enyl]benzoic acid (6.43 g) in THF (50 ml) containing 10% palladium on carbon (1 g) was stirred under an atmosphere of hydrogen (balloon) for 15 hours. The catalyst was removed by filtration and the residue obtained on removal of the solvent was purified by chromatography on silica, eluting with 5% methanol in dichloromethane, to give 4-[3-(2-benzylphenyl)propyl]benzoic acid, m.p. 135-6° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe residue obtained on removal of the solvent
  3. customwas purified by chromatography on silica
  4. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-3ae3170213a44ec2a5144b1284de5d83
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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