Triethylamine → 2-[2-(4-Methoxyphenyl)ethyl]benzoic acid

HRID 970051Notes

Reaction equation

HRID 970051 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH:7]=[C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:10](=[O:11])[O:9]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[H][H]>[Ni].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH2:8][C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:10]([OH:11])=[O:9])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 979553-(4-Methoxybenzylidene)phthalideHCID 178418361HCID 178418361, compound

Product 1

HCID 261887002-[2-(4-Methoxyphenyl)ethyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To 280 ml of an ethanol solution containing 20.0 g (79.3 mmol) of 3-(4-methoxybenzylidene)phthalide were added 16.6 ml (119 mmol) of triethylamine and Raney nickel (available from Kawaken Finechemical, developed nickel catalyst NTD-65, 24 ml), and the resulting mixture was stirred at 80° C. for 2.5 hours under pressure with hydrogen (10 atm).

Sources & evidence

ORD record
ord-2b0af96efca24957b795dbd9f747fd65
Source dataset
uspto-grants-2007_12
Patent number
US07309718B2

Reaction notes

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