sodium hydride in N,N-dimethyl-formamide T=100°C; 6 h;

N,N-dimethyl-formamide T=50°C; 1.5 h;

T=50°C; 1.5 h; other naphthoates and benzoates, other sodium alkoxides, var. temp., var. time; Product distribution;

1: 87 percent / benzene; diethyl ether / 1.) 2 h, room temperature, 2.) 3 h, reflux 2: N-bromosuccinimide (NBS), benzoyl peroxide (BPO) / CCl4 / 8 h / Heating 3: 1.) AcOK; 2.) 2 N HCl / 1.) AcOH, 8 h, reflux; 2.) reflux, 30 min 4: 97 percent / KMnO4 / acetone; H2O / 1.5 h / Heating 5: 78 percent / KOH / H2O / 2 h / Heating View Scheme

1: 87 percent / benzene; diethyl ether / 1.) 2 h, room temperature, 2.) 3 h, reflux 2: N-bromosuccinimide (NBS), benzoyl peroxide (BPO) / CCl4 / 8 h / Heating 3: 1.) AcOK; 2.) 2 N HCl / 1.) AcOH, 8 h, reflux; 2.) reflux, 30 min 4: 97 percent / KMnO4 / acetone; H2O / 1.5 h / Heating View Scheme