HCID 13723674, compound → HCID 13723663, compound

Participants

Reaction Steps

Jones' reagent (11.6 ml.) was added dropwise to a stirred solution of 6-acetyl-2-hydroxymethyl-1,4-benzodioxan (4.0 g.) in acetone (70 ml.) at 10°-15° C. The reaction was stirred at room temperature for 18 hours then diluted with isopropanol/water/chloroform, the organic layer separated and evaporated in vacuo. The residue was redissolved in chloroform, extracted with saturated sodium carbonate solution (2×30 ml.) then the basic phase washed with chloroform, cooled and acidified to pH 1 with concentrated hydrochloric acid. The acidic solution was extracted with chloroform, the combined extracts washed with saturated brine, dried (Na2SO4) and evaporated in vacuo to give 6-acetyl-1,4-benzodioxan-2-carboxylic acid (1.56 g.), m.p. 159°-162° C. A sample was recrystallized from ethanol/ethyl acetate, m.p. 174°-175° C.

Provenance & Evidence