hydrogen; Lindlar's catalyst in tetrahydrofuran; methanol 2 h;

sodium hydroxide in toluene T=0°C; 0.166667 h;

sodium hydroxide in toluene T=0°C; 0.25 h;

1: 78.8 percent / 16percent methanolic ammonia / methanol / 67 h / 5 °C 2: 59.3 percent / hydrogen / 10percent palladium on calcium carbonate / tetrahydrofuran; methanol / 2 h View Scheme

1: 74.4 percent / 1-hydroxybenzotriazole, triethylamine / dicyclohexylcarbodiimide / tetrahydrofuran; methanol / 16 h / Ambient temperature 2: 78.8 percent / 16percent methanolic ammonia / methanol / 67 h / 5 °C 3: 59.3 percent / hydrogen / 10percent palladium on calcium carbonate / tetrahydrofuran; methanol / 2 h View Scheme

1: aq. 2 N NaOH, ice / toluene 2: H2O (air) / 16 h / Ambient temperature View Scheme

water 16 h; Ambient temperature; Yield given. Yields of byproduct given;

toluene-4-sulfonic acid in ethanol 0.5 h; Heating;

toluene-4-sulfonic acid in ethanol 0.5 h; Heating;