Methanol → HCID 14668942, compound

Participants

Reaction Conditions

Reaction Steps

1,3-dioxane-4-ylmethylphthalimide (95 g, 390 mmol) was dissolved in a saturated solution of hydrochloric acid in methanol (600 mL) and stirred for 2 days at 80° C. The reaction was then cooled to room temperature, and the acid neutralised to pH 7 with solid NaHCO3. Ethyl acetate (1 L) was added and the mixture was filtered to remove salts. The filtrate was then concentrated under reduced pressure and dried overnight in vacuo. The crude was purified through a silica gel plug (1 kg silica) using 2:98 CH3OH:CH2Cl2 eluent to give the desired N-(2,4-dihydroxybutyl)phthalimide as a white solid (45 g, 50%). 1H NMR (MeOD) δ 1.62 (m, 1H), 1.75 (m, 1H), 3.31 (s, 1H), 3.64 (m, 2H), 3.69 (d, 2H, J=5.1 Hz), 4.06 (sept, 1H), 7.79 (m, 2H), 7.85 (m, 2H).

Provenance & Evidence