Sulfuric Acid → HCID 66969973, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6.00 mol/L H2SO4 (aq.) (700 mL) was added to a solution of compound G (65.7 g, 237 mmol) in 1,4-dioxane (700 mL) at room temperature. The mixture was heated at 130° C. (oil bath temperature) and stirred. After 64 h the mixture was concentrated in vacuo, and cooled to 0° C. The precipitate was filtered and rinsed with a small amount of water to give the desired compound H (23.8 g, 106 mmol) as an off-white solid. The filtrate was extracted twice with ethyl acetate and the combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo to give the desired compound H (10.8 g, 48.2 mmol) as an off-white solid. The aqueous phase (after salting with NaCl) was extracted with CHCl3/MeOH (4/1), and the combined organic phases were dried over Na2SO4 and concentrated in vacuo to recover the starting material G (26%). 1H NMR (DMSO-d6 400 MHz): δ 1.14 (3H, t, J=7.6 Hz), 2.60 (2H, q, J=7.6 Hz), 3.80 (3H, s), 7.04 (1H, d, J=2.4 Hz), 7.16 (1H, d, J=2.4 Hz). EIMS (+): 224 [M]+

Provenance & Evidence