Sodium Hydroxide → HCID 18988219, compound

Participants

Reaction Steps

Part B. A solution of the ester prepared in Part A above (1.68 g, 6.31 mmol) in ethanolic sodium hydroxide (60.0 mL, 0.25M in 95% ethanol, 15.0 mmol) was stirred at ambient temperature for 14 hours. The solution was evaporated, and the residue neutralized to pH 5 with 1N aqueous hydrochloric acid. This was diluted to 100 mL with water, and extracted with ethyl acetate (2×100 mL). The extracts were washed with brine, combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the product, 6,7-dimethoxy-1,2,3,4-tetrahydro-2-thianaphthalene-1-carboxylic acid, as an oil (1.42 g, 5.96 mmol, 94%). 1H NMR (CDCl3): δ 7.06 (1H, s); 6.62 (1H, s); 5.30 (1H, s); 4.34-4.24 (1H, m); 4.02-3.92 (1H, m);3.87 (6H, s); 2.94-2.72 (2H, m). Mass spectrum (NH3 -CI/DDIP): m/z 241(2%); 240 (11%); 239 (87%); 221 (8%); 193 (100%).

Provenance & Evidence