Hexanoic Acid → Hexanoyloxymethyl p-nitrophenyl carbonate

Participants

Reaction Steps

A solution of 0.25 g of iodomethyl p-nitrophenyl carbonate and 0.5 g hexanoic acid was heated to reflux in benzene with 0.5 g of silver hexanoate. After two hours the reaction mixture was filtered, and the filtrate was washed successively with aqueous sodium bicarbonate and water. After drying over sodium sulfate, the solvent was evaporated to furnish hexanoyloxymethyl p-nitrophenyl carbonate as a light yellow liquid (0.28 g). IR (film) 1775 (C=O). NMR (CDCl3) 0.9 (t, 3H, J=7 Hz, Me), 1.1-2.0 (m, 6H, (CH2)3), 2.41 (t, 2H, J=7 Hz, COCH2), 5.88 (s, 2H, OCH2O), 7.38 (d, 2H, J=10 Hz, aromatic), 8.21 (d, J=10 Hz, 2H, aromatic).

Provenance & Evidence