Sodium Hydroxide → HCID 68840681, compound

Reaction equation

C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH:15]=[CH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[C:19]1([CH2:18][CH2:17][CH:16]=[CH:15][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:13]=[CH:14][C:5]=2[C:3]([OH:4])=[O:2])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Procedure

175 mg 1-(4-phenyl-but-1-enyl)-naphthalene-2-carboxylic acid methyl ester were reacted with 1 ml of 2 M aqueous sodium hydroxide in 1.5 ml methanol and 4 ml THF for 1 h at 60° C. The organic solvents were removed in vacuo, the mixture was acidified with 2 M hydrochloric acid and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated to yield 165 mg of a mixture of the (E)- and (Z)-isomers of 1-(4-phenyl-but-1-enyl)-naphthalene-2-carboxylic acid.