Triethylamine → 3,4-Bis(acetyloxy)benzenesulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

To a solution of the crude, 3,4-diacetoxy benzene sulphonic acid (0.83 g) in a mixture of sulpholane (1.5 ml) and acetonitrile (1.5 ml) was added at room temperature successively N,N-dimethylacetamide (75 μl), triethylamine (0.85 ml) and phosphorus oxychloride (1.1 ml). The reaction mixture was thereafter heated for 15 minutes at 70° C., cooled, poured onto water and extracted with CH2Cl2. The extract was dried over magnesium sulphate, concentrated and chromatographed on silica gel (50 g). Elution with CH2Cl2 gave 0.65 g (74%) of the title compound as a white solid. NMR in CDCl3 : 2.33(s,6H); 7.29(d,1H); 7.90(s,1H); 7.95(dd,1H).

Provenance & Evidence