1: SOCl2 / benzene / 4 h 2: diethyl ether / Ambient temperature View Scheme

1: 92 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) room temperature, 2 h 2: 90 percent / thionyl chloride, pyridine / diethyl ether / 2 h / 0 °C 3: 5percent NaOH / ethanol / 2 h / Heating 4: SOCl2 / 4 h 5: diethyl ether View Scheme

1: 90 percent / thionyl chloride, pyridine / diethyl ether / 2 h / 0 °C 2: 5percent NaOH / ethanol / 2 h / Heating 3: SOCl2 / 4 h 4: diethyl ether View Scheme

1: 5percent NaOH / ethanol / 2 h / Heating 2: SOCl2 / 4 h 3: diethyl ether View Scheme

in diethyl ether Yield given;