p-Anisoyl chloride → 4,5-Dihydro-2-(4-methoxyphenyl)-4,4-dimethyloxazole

Participants

Reaction Steps

A solution of 2-amino-2-methyl-propan-1-ol (104.5 g, 1.17 moles) in CH2Cl2 (400 ml) under N2 was dropwise added in 30 minutes with a solution of 4-methoxybenzoyl chloride (100 g, 0.59 moles) in CH2Cl2 (500 ml), keeping the temperature at about 18° C. with water/ice. After 3 hours under stirring the precipitate was filtered over celite and washed with CH2Cl2. The organic phase was stirred under N2 at 2° C. and dropwise added with thionyl chloride (123 ml, 1.77 moles), keeping the temperature below 10° C. At the end of the dropping the reaction mixture was stirred overnight, then concentrated under vacuum. The residue was taken up in 5% HCl and twice extracted with ethyl ether. The extracts were in turn extracted with 5% HCl. The aqueous phase was alkalinised with concentrated NaOH and extracted three times with ethyl ether, then anhydrified and concentrated under vacuum. The crude was distilled at 95-98° C. (30 Pascal) to give 106.43 g of the title compound (yield: 87.6%).

Provenance & Evidence