Methyl dichloroacetate → HCID 66929700, compound

Participants

Reaction Steps

31.0 g of 4-nitrocatechol was added to 17.6 g of 60% NaH in suspension in 300 ml of DMF over 1 hour, with cooling to keep the temperature below 30° C. Stirring was continued for 15 minutes then 104 ml of methyl dichloroacetate was added over 1 hour, and stirring was continued for 4 hours at 90° C. The reaction medium was poured over a mixture of 2 liters of ice/water then extracted 4 times with 400 ml of AcOEt. The combined organic phases were washed once with a saturated NaCl solution then dried and concentrated under vacuum (DMF evaporated off). The residue was taken up in a AcOEt/H2O mixture and the pH was brought to 8.6 using Na2CO3; the organic phase was decanted, washed with saturated NaHCO3, H2O, 5% KHSO4/K2SO4, H2O, saturated NaCl then dried and vacuum evaporated; a semi-solid residue was obtained which was taken up then triturated in heptane to produce a solid. m=27.7 g, MP=90-92° C.

Provenance & Evidence