Hydrochloric Acid → 1-Hydroxy-3-methyl-1-(4-nitrophenyl)-6-methoxyisochroman

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A solution of 3 (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 phase was washed with water in order to remove DMF, dried over Na2SO4. Removal of the solvent afforded syrup crude product (1.6 g), which was used directly for the next step.

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