1: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 2: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 3: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

1: 89 percent / (COCl)2 / benzene / 2 h, room t., 1 h, reflux 2: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 3: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 4: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 5: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

1: 70 percent / NaOAc, H2 / 10percent Pd-C / 2427.2 Torr / 1h, then 60 degC, overnight 2: 1.) Mg; MeI / diethyl ether / 1.) 3 h, reflux; 2.) 1 h, reflux 3: hydrogen, conc. H2SO4 / 10percent Pd-C / ethyl acetate / 4 h / 2942.03 Torr / Ambient temperature 4: NaI, ClSiMe3 / acetonitrile / 36 h / Heating View Scheme

hydrogen bromide; acetic acid

1: aq. NaOH / methanol / 24 h / Ambient temperature 2: H2O; methanol / 5 h / 60 °C View Scheme

sodium hydroxide

acetic acid