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

HRID 1106840Notes

Reaction equation

HRID 1106840 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-7b32bb356b0640d38b4d8e25ce4e23e8
Source dataset
uspto-grants-2000_05
Patent number
US06057345

Reaction notes

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