1: 57 percent / chloranil / xylene / 2 h / Heating 2: NaBH4, CoCl2 / methanol / 0.5 h / 0 °C 3: pyridine / 1 h / Ambient temperature 4: 94 mg / POCl3 / toluene / 1 h / Heating View Scheme

1: 57 percent / chloranil / xylene / 2 h / Heating 2: NaBH4, CoCl2 / methanol / 0.5 h / 0 °C 3: pyridine / 1 h / Ambient temperature 4: 94 mg / POCl3 / toluene / 1 h / Heating 5: 82 percent / 10percent palladium on carbon / decahydronaphthalene / 1.5 h / Heating View Scheme

1: 57 percent / chloranil / xylene / 2 h / Heating 2: NaBH4, CoCl2 / methanol / 0.5 h / 0 °C 3: pyridine / 1 h / Ambient temperature View Scheme

1: 57 percent / chloranil / xylene / 2 h / Heating 2: NaBH4, CoCl2 / methanol / 0.5 h / 0 °C View Scheme

With  disodium hydrogenphosphate; sodium amalgam in  tetrahydrofuran; methanol T=25°C; 4 h;   

Multi-step reaction with 2 steps 1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) -78 deg C, 30 min2: 90 percent / Na(Hg), Na2HPO4 / methanol; tetrahydrofuran / 4 h / 25 °C