Sodium Hydroxide → HCID 18988219, compound

Participants

Reaction Conditions

Reaction Steps

Part D. The ester compound from Part C above (1.88 g, 6.66 mmol) was stirred in ethanolic sodium hydroxide solution (0.25N, 60.0 mL, 15.0 mmol)for 14 hours. The mixture was evaporated, and the residue was taken up in 1N aqueous sodium hydroxide (120 mL). This solution was washed with ether (2×120 mL), then cooled to 0° C. and neutralized to pH 5 with6N aqueous hydrochloric acid. This was then extracted with ethyl acetate (2×120 mL), and the extracts were 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 asolid, mp 167°-169° C. (1.66 g, 6.53 mmol, 98%). 1H NMR(CDCl3): δ 6.63 (2H, s); 4.43 (1H, s); 3.86 (3H, s); 3.85 (3H, s); 3.34 (1H, ddd, J=13.8, 8.0, 5.2 Hz); 3.09 (1H, dd, J=10, 4.5 Hz); 3.03(1H, dd, J=10, 4.9 Hz); 2.74 (1H, dt, J=13.8, 4.7 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 272 (100%); 256 (1%); 255 (8%); 209 (3%); 106 (1%).

Provenance & Evidence