trifluoroacetic acid; phenol; palladium on activated charcoal T=50°C; 3 h;

2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 12 h; Heating;

1.1: 55 percent / acetone / 168000 h / 20 °C 2.1: LDA / cyclohexane; tetrahydrofuran / 0.5 h / -78 °C 2.2: cyclohexane; tetrahydrofuran / -78 - -40 °C 2.3: 70 percent / Et3N / cyclohexane; tetrahydrofuran / 12 h / 20 °C 3.1: MeONa / tetrahydrofuran / 0.02 h / 20 °C 4.1: 1.13 g / Ph3SnH; AIBN / benzene / 3 h / Heating 5.1: 50 percent / phenol; TFA / Pd/C / 50 °C View Scheme

1: triethylamine / tetrahydrofuran / 0 °C 2: 1.9 g / MeONa / tetrahydrofuran / 0.05 h / 20 °C 3: 80 percent / phenol; TFA / 10 percent Pd/C / 3 h / 50 °C View Scheme

1: 1.9 g / MeONa / tetrahydrofuran / 0.05 h / 20 °C 2: 80 percent / phenol; TFA / 10 percent Pd/C / 3 h / 50 °C View Scheme

sulfuric acid 1.25 h; Heating;

1: 70 percent / sodium methoxide / toluene / 48 h / Ambient temperature 2: 69 percent / 2 N H2SO4 / 1.25 h / Heating View Scheme

1: With water; sodium hydroxide in methanol T=20°C; 1 h; 2: With hydrogenchloride in water pH=~ 2;