Methanol → HCID 66733598, compound

Participants

Reaction Steps

3.0 g (11.9 mmol) of compound of example 9 and 1.22 g (3.6 mmol, 0.3 eq.) tetrabutylammonium hydrogen sulphate is suspended in 20 ml of dichloromethane. The suspension is refluxed, under vigorous stirring, until a homogenous solution is obtained. To this solution p-methylbenzyl chloride (7.23 ml, 53.6 mmol, 4.5 eq) followed by 5 ml of 50% (w/w) NaOH solution are added. The thick emulsion is refluxed for 3 hours while vigorously stirred, then 8 ml of MeOH are added and the reaction mixture is additionally refluxed for one night. After cooling DCM and water are added. The phases are separated and the aqueous phase is washed with DCM. The combined organic phases are washed with brine and the solvents are evaporated. The crude product is purified by column chromatography. The purest fractions are collected and the product is recrystallized from MeOH to yield 2.0 g of white solid. M.p.: 84-85° C.

Provenance & Evidence