Dimethyl Sulfate → HCID 22452654, compound

Participants

Reaction Steps

To a stirred suspension of 4-iodo-3-hydroxy-5,6,7,8-tetrahydro-2-naphthalenecarboxylic acid (23.43 g, 73.65 mmol) in dry acetone (450 mL) was added dimethyl sulfate (17.42 mL, 184.13 mmol) and K2CO3 (25.45 g, 184.13 mmol). The mixture was stirred at reflux overnight, cooled and triethylamine (40 mL) was added. After 0.5 h the mixture was filtered through a pad of diatomaceous earth and the filtrate concentrated in vacuo. The residue was dissolved in ethyl acetate (50 mL) and washed successively with 1N HCl (2×50 mL), sat. aqueous sodium bicarbonate (2×50 mL) and brine (50 mL ), dried (Na2SO4), filtered and concentrated in vacuo to afford a brown oil (22.52 g, 90%). 1H NMR (CDCl3) δ 7.56 (s, 1H), 3.92 (s, 3H), 3.85 (s, 3H), 2.69 (m, 4H), 1.79 (m, 4H). MS m/z 347 (M+H).

Provenance & Evidence