Water → Methyl 4-(chloromethyl)benzoate

Participants

Reaction Steps

Stir a mixture of 100 g of the product prepared as described in step (a)in 500 mL of dry DMF and 81.1 g (0.54168 moles) of Nal and 150 g (0.8108 moles, 1.5 eg) of sodium 2,6-dichlorophenoxide at room temperature overnight. Add water to the so-formed formed reaction mixture to produce a precipitated solid. Add CH2Cl2 to dissolve the precipitated solid. Wash the CH2Cl2 layers successively with four volumes of a 5% aqueous NaOH solution, water and brine. Separate and dry the organic layer over Na2SO4. Remove the solvent under reduced pressure to produce 164.5 g (97.6% of theory) of the title compound. The 200 MHzNMR spectrum is consistent with the proposed ester structure ##STR121##

Provenance & Evidence