hydrogen iodide; phenol T=145°C; 0.5 h;

aluminum tri-bromide in acetonitrile T=25 - 28°C; 2 h;

1: 1.) potassium 3,4-bis(benzyloxy)benzoate, 2.) aq. KOH / 1.) 170 - 180 deg C, 8 h, 2.) methanol, acetone, water, reflux, 20 min 2: 95 percent / H2 / 10percent Pd/C / methanol; ethyl acetate 3: 65 percent / AlBr3 / acetonitrile / 2 h / 25 - 28 °C View Scheme

1: 1.) potassium 3,4-bis(benzyloxy)benzoate, 2.) aq. KOH / 1.) 170 - 180 deg C, 8 h, 2.) methanol, acetone, water, reflux, 20 min 2: 95 percent / H2 / 10percent Pd/C / methanol; ethyl acetate 3: 65 percent / AlBr3 / acetonitrile / 2 h / 25 - 28 °C View Scheme

1: 95 percent / H2 / 10percent Pd/C / methanol; ethyl acetate 2: 65 percent / AlBr3 / acetonitrile / 2 h / 25 - 28 °C View Scheme

hydrogenchloride; aluminum tri-bromide 1.) CH3CN, 25-28 deg C, 2 h, 2.) MeOH, reflux, 4.5 h; Yield given. Multistep reaction. Yields of byproduct given;