Hydrochloric Acid → HCID 67415276, compound

A solution of borane in tetrahydrofuran (1M in tetrahydrofuran, 27.1 mL, 27.1 mmol) was added dropwise to a solution of 3,5-dimethyl-4-hydroxybenzonitrile (1.0 g, 6.79 mmol) in tetrahydrofuran (70 mL) and the resulting solution was heated under reflux for 16 hours. The reaction mixture was cooled to room temperature, treated with 6N hydrochloric acid (20 mL) and heated under reflux for a further 30 minutes. The reaction mixture was then cooled to room temperature and the solvent was removed in vacuo. The residue was purified using a strong cation exchange resin eluting with methanol followed by 2M ammonia in methanol, to give an orange oil. This oil was then treated with 1M hydrogen chloride in methanol (20 mL) and the reaction mixture was concentrated in vacuo to afford the title compound as a pale yellow solid in quantitative yield, 1.12 g. 1HNMR (400 MHz, CDCl3) δ: 2.22 (6H, s), 3.75 (2H, s), 6.90 (2H, s).

1. temperaturethe resulting solution was heated
2. temperatureunder reflux for 16 hours
3. temperatureheated
4. temperatureunder reflux for a further 30 minutes
5. temperatureThe reaction mixture was then cooled to room temperature
6. customthe solvent was removed in vacuo
7. customThe residue was purified
8. washeluting with methanol
9. customto give an orange oil
10. concentrationthe reaction mixture was concentrated in vacuo

ORD record

ord-603a93c14c934ab9be3386291f5007b8

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547731B2