Hydrochloric Acid → (7-Methoxy-1,3-benzodioxol-5-yl)methanol

Methyl 7-methoxybenzo[3,4-d]1,3-dioxolane-5-carboxylate(10 g, 47.57 mmol) prepared in Step 3 was dissolved in tetrahydrofuran(200 ml), borane methylsulfide(BMS, 10M) (9.5 ml, 95.0 mmol) was added thereto, and the mixture was stirred under reflux for 1.5 hour. The reaction vessel was cooled down to room temperature and the reaction mixture was neutralized to pH 6-7 using 1N—HCl at 0-5° C., which was then extracted with ethyl acetate. The extract was washed with saturated saline solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2, v/v) to give (7-methoxybenzo[3,4-d]1,3-dioxolan-5-yl)methan-1-ol(7.63 g, Yield 88%) as a white solid.

1. temperatureunder reflux for 1.5 hour
2. customat 0-5° C.
3. extractionwhich was then extracted with ethyl acetate
4. washThe extract was washed with saturated saline solution
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated

ORD record

ord-62f7d0df5d624a348982cb5594475059

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06693126B2