1: 1) potassium 3,4-dibenzyloxybenzoate, 2) aq. KOH / 1) 160 deg C, 8 h, 2) MeOH, reflux 2: 99 percent / cyclohexene / Pd(OH)2/C / ethanol / 0.5 h / Heating View Scheme

1: 1.) potassium benzoate, 2.) K2CO3 / 1.) 170/180 deg C, 8 h, 2.) acetone, reflux, 2.5-4 h 2: 90 percent / AlBr3 / acetonitrile / 0.33 h / 0 - 5 °C 3: 99 percent / K2CO3 / acetone / Heating 4: 90 percent / AlBr3 / acetonitrile / 1 h / Ambient temperature 5: 87 percent / K2CO3 / methanol / 2 h / Heating 6: 94 percent / H2 / 10percent palladium on charcoal / ethyl acetate; methanol 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