Methanol → Methyl 3-(5-hydroxypyrimidin-2-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

78.8 g of 3-(5-hydroxypyrimidin-2-yl)benzoic acid are suspended in 1.4 l of absolute methanol, and 32.7 ml of thionyl chloride (449.8 mmol) are subsequently carefully added dropwise at RT. The reaction batch is warmed at 80° C. for 2 h. A further 20 ml of thionyl chloride (275.7 mmol) are added, and the mixture is warmed at 80° C. for a further 2 h. In order to complete the reaction, a further 10 ml of thionyl chloride (137.8 mmol) are added, and the mixture is warmed at 80° C. for a further 2 h. For work-up, 1000 ml of methanol are removed in a rotary evaporator, and the resultant residue is filtered off. The mother liquor is reduced to about 200 ml in the rotary evaporator, and the crystals formed are filtered off. The two crystal batches are combined, dried to constant weight at 50° C. in a vacuum drying cabinet.

Provenance & Evidence