Calcium Carbonate → HCID 86756225, compound

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Reaction Steps

To a suspension of N-[4-hydroxy-2,3,6-trimethyl-5-(2-methyl-2-propenyl)phenyl]formamide (187 g) and calcium carbonate (104 g) in tetrahydrofuran (600 mL) and methanol (600 mL) was added benzyltrimethylammonium dichloroiodate (307 g) slowly. The mixture was stirred for 10 minutes. The insoluble material was removed by filtration and the filtrate was concentrated in vacuo. To the residue was added ethyl acetate (800 mL) and water (400 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (400 mL). The combined organic layer was washed with 10% aqueous solution hydrogen sulfite (400 g), water (300 mL), saturated aqueous sodium bicarbonate (300 mL) and aqueous sodium chloride (300 mL). The organic layer was dried over magnesium sulfate, treated with activated carbon, filtrated and the filtrate was concentrated in vacuo. The residue was crystallized from ethyl acetate/diisopropyl ether to afford 271 g of the title compound. Yield 94%.

Provenance & Evidence