1: 76 percent / sodium ethoxide / toluene / 21 h 2: 23 percent / BTMG / tetrahydrofuran / 21 h / Ambient temperature View Scheme

1: NaBH4 2: 76.3 percent / toluene-p-sulphonic acid / benzene / 0.5 h / 45 °C View Scheme

1: NaBH4 2: 76.3 percent / toluene-p-sulphonic acid / benzene / 0.5 h / 45 °C 3: 1.) mercury(II) acetate, 2.) lithium chloride, 3.) palladium dichloride, lithium chloride / 1.) methanol, room temperature, 2 h, 2.) acetone, 15 min 4: 85.6 percent / H2 / 10percent palladium-charcoal / acetone 5: 57.6 percent / sodium methoxide / methanol 6: 71.5 percent / m-chloroperbenzoic acid, toluene-p-sulphonic acid (trace) 7: 39 mg / toluene-p-sulphonic acid View Scheme

Multi-step reaction with 5 steps 1: NaBH4 2: 76.3 percent / toluene-p-sulphonic acid / benzene / 0.5 h / 45 °C3: 1.) mercury(II) acetate, 2.) lithium chloride, 3.) palladium dichloride, lithium chloride / 1.) methanol, room temperature, 2 h, 2.) acetone, 15 min4: 85.6 percent / H2 / 10percent palladium-charcoal / acetone5: 57.6 percent / sodium methoxide / methanol  

With  sodium methylate in  benzene 1 h;   

With  sodium ethanolate in  toluene 21 h;