Water → HCID 58463234, compound

Participants

Reaction Steps

To a solution of 4-methylbenzaldehyde (0.70 g) and dimethyl succinate (0.95 g) in tetrahydrofuran (15 mL) was added potassium tert-butoxide (0.73 g) at room temperature, and the reaction mixture was stirred overnight. To the reaction mixture were added water and diethyl ether, and the two layers were separated. The aqueous layer was acidified with 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. This organic layer was washed with a saturated sodium carbonate aqueous solution. The aqueous layer was acidified with 1 mol/L hydrochloric acid, and the mixture was extracted with diethyl ether. The organic layer was dried over magnesium sulfate, and concentrated. To the residue were added acetic acid (5 mL), acetic anhydride (5 mL) and sodium acetate (3.0 g), and the mixture was heated under reflux for 6 hours. After cooling to room temperature, the reaction mixture was poured into water. The resulting mixture was extracted with diethyl ether. The organic layer was washed with water and a saturated sodium hydrogen carbonate aqueous solution, and concentrated. To the obtained residue were added methanol (20 mL) and 1 mol/L sodium hydroxide aqueous solution (20 mL), and the mixture was heated under reflux for 5 hours. After the reaction mixture was cooled to room temperature, methanol was removed under reduced pressure. The obtained solution was acidified with 2 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to give the title compound (0.20 g).

Provenance & Evidence