1: H2 / 10percent Pd on charcoal / ethyl acetate / 72 h / 2844.3 Torr 2: 86 percent / 1.) AlCl3, 2.) ice / CS2 / 1.) 0 deg C then RT 2 h 3: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 20 h / Heating 4: NaBH4 / methanol / 2 h View Scheme

sodium tetrahydroborate in methanol 2 h; Yield given;

1: 86 percent / 1.) AlCl3, 2.) ice / CS2 / 1.) 0 deg C then RT 2 h 2: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 20 h / Heating 3: NaBH4 / methanol / 2 h View Scheme

1: 93 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 20 h / Heating 2: NaBH4 / methanol / 2 h View Scheme

1: 79 percent / p-toluenesulfonic acid / benzene / 20 h / Heating 2: 63 percent / m-chloroperbenzoic acid / tetrahydrofuran / 5 h View Scheme

toluene-4-sulfonic acid in benzene 20 h; Heating;