Methanesulfonyl chloride → Methyl 4-(chloromethyl)benzoate

Participants

Reaction Steps

To a solution of 100 g (0.60175 moles) of methyl 4-hydroxymethylbenzoate in 600 mL of dry CH2Cl2. add 109 mL (79.1 g) of TEA and cool the so-formed reaction mixture to 0° C. Add, dropwise over a 2 hour period, 55.8 mL (0.722 mole, 1.2 eq) of methanesulfonyl chloride in 150 mL of dry CH2Cl2. Allow the so-formed stirred reaction mixture to warm slowly to room temperature over a 48 hr period. TLC shows no starting material remains. Add water, separate the layers and wash the organic layer successively with water, saturated NaHCO3 and brine. Dry the organic layer over Na2SO4. Remove the organic solvent under reduced pressure to produce 98.45 g of (88.6 % of theory) of the title compound as a crystalline solid. ##STR120##

Provenance & Evidence