Potassium Hydroxide → Ro 40-6055
Reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([NH:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2.[OH-].[K+]>CO>[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 25 mL round bottom flask equipped with a reflux condenser was charged with methyl methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoate 3 (0.200 g, 0.547 mmol), MeOH (10 mL) and KOH (0.122 g, 2.18 mmol). The reaction mixture was stirred for 16 h at reflux, evaporated to dryness and partitioned between EtOAc and H2O. 6N HCl was added until pH became acidic and the organic layer was separated, washed with water, brine, dried with Na2SO4, filtered and concentrated on a rotary evaporator to give 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoic acid 4 as a white solid (0.151 g, 78%).