hydrogenchloride in ethanol

triphenylphosphine; diethylazodicarboxylate in dichloromethane Mitsunobu reaction;

1.1: acetic acid; bromine / 2 h / 20 °C 2.1: potassium carbonate / acetone / |Reflux 3.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation 4.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 4.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 4.3: 2 h / |Reflux 5.1: potassium carbonate / acetone / 4 h / |Reflux 6.1: ethanol / 14 h / |Reflux 7.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 8.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 9.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 10.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 11.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 12.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 13.1: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme

diisobutylaluminium hydride in toluene T=-78°C; 5 h;

1: chloroform; bromine 2: aq. NaOH solution 3: ethanolic KOH-solution View Scheme

1: methyl [4-hydroxyphenyl]acetate With potassium carbonate in DMF (N,N-dimethyl-formamide) T=20°C; 1 h; 2: 2-methyl-1-bromopropane in DMF (N,N-dimethyl-formamide) T=80°C; 72 h; 3: With hydrogenchloride; potassium hydroxide more than 3 stages;

1.1: K2CO3 / dimethylformamide / 0.5 h / 20 °C 1.2: dimethylformamide / 20 - 50 °C 2.1: 82 percent / aq. NaOH / ethanol / 20 °C View Scheme

1: 90 percent / NaBH4 / H2O / 8 h / Ambient temperature 2: 73 percent / 1N aq. NaOH / tetrahydrofuran / 1 h / Ambient temperature 3: 1.) Ag2CO3, Drierite, 2.) I2 / 1.) Et2O, RT, 10 min, 2.) Et2O, RT, 14 h 4: 97.7 percent / NaOMe / methanol / 1 h / Ambient temperature View Scheme

in water

1: acetic acid; bromine / 2 h / 20 °C 2: potassium carbonate / acetone / |Reflux 3: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation View Scheme