Dichloromethane → 3,6-Bis(chloromethyl)toluene

Participants

Reaction Steps

A 200 ml round-bottomed flask was charged with the entire amount (2.7 g) of the above 2,5-bis(hydroxymethyl)-toluene, and 60 ml of dichloromethane was added thereto and suspended therein by stirring the mixture. Added dropwise thereto was 4 ml (5.5 mmol) of thionyl chloride, and the resultant mixture was stirred at room temperature for 3 hours and subjected to extraction by adding 50 ml of water. An organic layer formed was washed with water and with salt water, and the solvent was distilled off. The residue was purified by silica gel column chromatography using 30 g of silica gel to give 2.5 g (13 mmol) of 2,5-bis(chloromethyl)-toluene (yield 72%). 2.3 Grams (12 mmol) of this 2,5-bis(chloromethyl)toluene and 6.6 g (26.4 mmol) of triphenylphosphine were added to 45 ml of DMF, and the resultant mixture was stirred under heat at 130° C. for 2 hours. After the reaction mixture was allowed to cool, a white powder formed was separated by filtering, and washed twice with 10 ml of DMF and 20 ml of ether to give 7.9 g of white crystals of 2-methylxylylenebistriphenylphosphonium chloride (yield 95%).

Provenance & Evidence