Hydrochloric Acid → HCID 20150417, compound

Participants

Reaction Conditions

Reaction Steps

The crude 3,4-dihydro-2-(3-hydroxypropyl)-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran (5.0 g) obtained in the above manner was dissolved in 50 ml of pyridine and the solution was cooled to 0° C. To the solution was added slowly 3.9 g of p-toluenesulfonyl chloride with vigorous stirring. After stirring at 0° C. for 1 hour, the reaction mixture was poured into 100 ml of dilute hydrochloric acid and extracted with diethyl ether. The ether layer was washed with water and then with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and filtered. Low-boiling substances were distilled off from the filtrate under reduced pressure. The residue was purified by silica gel column chromatography to give 3.8 g of 3,4-dihydro-6-methoxy-2-[3-(p-toluenesulfonyloxy)propyl]-2,5,7,8-tetramethyl-2H-benzopyran.

Provenance & Evidence