Ethyl Acetate → 2,3-Dihydrothieno(3,4-b)-1,4-dioxin-2-methanol

Participants

Reaction Conditions

Reaction Steps

2-Hydroxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxine-5,7-dicarboxylic acid (48 g, 0.184 mol) was dissolved in N,N-dimethylacetamide (500 mL), and Cu2Cr2O7 (8.6 g) and quinoline (15 drops) were added. This mixture was subsequently stirred for 2 hours at 150° C., after which it was cooled to 25° C. It was then poured into ethyl acetate, the catalyst removed by filtration and the filtrate washed with acidic water and a saturated aqueous solution of sodium chloride. The solvent was then removed after which pure (2,3-dihydro-thieno[3,4-b][1,4]dioxin-2-yl)-methanol was isolated by vacuum distillation (115-120° C.; 0.05 mm Hg).

Provenance & Evidence