1.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C 2.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C 2.2: 62 - 66 °C / Inert atmosphere 3.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux 3.2: 20 °C 4.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C 4.2: 2 - 51 °C 5.1: boron trichloride / dichloromethane / 52.25 h / 2 - 20 °C 5.2: 1.08 h / 12 °C / Reflux View Scheme

acetic acid

acetic acid Product distribution / selectivity;

1: potassium carbonate / tetra(n-butyl)ammonium hydrogensulfate / ethyl acetate; water / 3 h / 13 - 35 °C / Reflux 2: acetic acid View Scheme

1: potassium carbonate / tetra(n-butyl)ammonium hydrogensulfate / ethyl acetate; water / 3 h / 13 - 35 °C / Reflux 2: acetic acid View Scheme

diethyl ether; magnesium anschliessend Behandeln mit CO2;

Oxydation;

1.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C 2.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C 2.2: 62 - 66 °C / Inert atmosphere 3.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux 3.2: 20 °C 4.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 16 h / 20 °C 4.2: 2 - 51 °C View Scheme

1.1: thionyl chloride / N,N-dimethyl-formamide / toluene / 5 h / 65 - 70 °C 2.1: iron(III) sulfate pentahydrate; iron / toluene / 99 - 114 °C 2.2: 62 - 66 °C / Inert atmosphere 3.1: sodium hydroxide / tetrabutylammomium bromide / toluene; water / 6 h / Reflux 3.2: 20 °C 4.1: sodium hydroxide / dichloromethane; water / 6.75 h / 16 - 20 °C / Reflux View Scheme