1: 1.) DIBAH, 2.) Jones reagent / 1.) toluene, -78 deg C, 4 h, 2.) acetone, room temp., 15 min 2: 70percent t-butyl-hydroperoxide, 40percent benzyltrimethylammonium hydroxide / benzene / Ambient temperature 3: p-toluenesulfonic acid / CH2Cl2 / 2 h 4: 100 percent / boron tribromide / CH2Cl2 / 0.25 h View Scheme

1: 1-bromo-4-methoxy-benzene With magnesium in tetrahydrofuran 2: perinaphthenone in tetrahydrofuran T=-70 - 20°C; 3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane 3 h; Heating;

1: 1-bromo-4-methoxy-benzene With iodine; magnesium in tetrahydrofuran 2: perinaphthenone in tetrahydrofuran T=-70 - 5°C; Grignard reaction; 3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane 0.166667 h; Heating;

2,3-dicyano-5,6-dichloro-p-benzoquinone 1.) ether, reflux, 3 h, 2.) CH2Cl2, reflux, 3 h; Yield given. Multistep reaction;