Hydrochloric Acid → 1-Hydroxy-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

Participants

Reaction Steps

A solution of 16 (1.3 g) in 4 ml of DMSO and 24 ml of DMF was cooled to 8-12° C. and air was passed through the mixture. To the solution was added 1.2 ml of 50% aqueous sodium hydroxide in one portion and the resulting mixture was stirred for 5 hours. HCl (1 N) was added, and extracted with ethyl acetate three times. The combined organic phases were washed with water, dried over Na2SO4. Removal of the solvent afforded 17 as a syrup (1.6 g), which was used directly for the next step.

Provenance & Evidence