Hydrochloric Acid → (3-Methoxy-1,2-phenylene)dimethanol

Temperature

0 °C

To a solution of 4-methoxy-1-(3H)-isobenzofuranone (described in J. Org. Chem., 52, 129 (1987); 1.64 g, 10.0 mmol) in tetrahydrofuran (30 ml) was added lithium borohydride (652.2 mg, 30 mmol) with stirring at 0° C., and the mixture was heated under reflux for 2.5 hours with stirring. After cooling the mixture to room temperature, a 2N aqueous solution of hydrochloric acid (20 ml) was added thereto. The product was extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium chloride. The filtrate was concentrated under reduced pressure to give a solid residue. The residue was subjected to chromatography on a silica gel (30 g) column (eluent; ethyl acetate:hexane=2:1˜4:1) to afford the title compound (1.31 g, 78% yield) as a colorless solid (mp. 95° C.).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 2.5 hours
3. stirringwith stirring
4. temperatureAfter cooling the mixture to room temperature
5. extractionThe product was extracted with ethyl acetate
6. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
7. concentrationThe filtrate was concentrated under reduced pressure
8. customto give a solid residue

ORD record

ord-00a765a01b1a4cf9a5afacf95d3269b9

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07230023B2