Hydrochloric Acid → HCID 54478410, compound

Participants

Reaction Steps

137 ml (137 mmol) of 1N hydrochloric acid, and 683 ml of methanol were added to 21.15 g (45.5 mmol) of 2,2-bis[(tert-butyldimethylsilyloxy)methyl]cyclopropylmethyl benzoate, and the solution was stirred for 40 minutes at room temperature. The solvent was distilled off, and the resulting oily product was purified by silica gel column chromatography (4% methanol/dichloromethane) to obtain 10.91 g (45.5 mmol, 100%) of 2,2-bis(hydroxymethyl)cyclopropyl methylbenzoate. This was a colorless oil; 1H-NMR (CDCl3) δ: 0.52 (dd, J=5.4, 5.4 Hz, 1H), 0.82 (dd, J=5.1, 8.7 Hz, 1H), 1.41 (m, 1H), 2.95 (broad s, 2H), 3.55 (d, J=11.4 Hz, 1H), 3.66 (d, J=11.4 Hz, 1H), 3.69 (d, J=12.0 Hz, 1H), 4.03 (d, J=12.0 Hz, 1H), 4.29 (dd, J= 8.7, 12.0 Hz, 1H), 4.57 (dd J=6.3, 12.0 Hz, 1H), 7.44 (m, 2H), 7.56 (m, 1H), 8.04 (m, 2H); FD MASS, M/z 236 (M+).

Provenance & Evidence