3-Hydroxybenzoic Acid → Cyclohexanecarboxylic acid, 3-hydroxy-

Temperature

150 °C

A 1 L pressure tank reactor (60 atm) containing a solution of 3-hydroxybenzoic acid (30 g, 217.20 mmol, 1.00 equiv), Raney Ni (5 g) and sodium hydroxide (6.4 g, 160.00 mmol, 0.74 equiv) in water (500 mL) was introduced H2 (gas, 60 atm) and the resulting solution was stirred overnight at 150° C. After completion of the reaction, the reaction temperature was cooled down to room temperature and the solids were filtered out by filtration. The resulting solution was neutralized with 12 M HCl, extracted with 6×100 mL of tetrahydrofuran. The combined organic layers were dried over sodium sulfate and concentrated under vacuum to provide 3-hydroxycyclohexane-1-carboxylic acid (11 g, crude) as a white solid.

1. additionwas introduced H2 (gas, 60 atm)
2. customAfter completion of the reaction
3. temperaturethe reaction temperature was cooled down to room temperature
4. filtrationthe solids were filtered out by filtration
5. extractionextracted with 6×100 mL of tetrahydrofuran
6. dry with materialThe combined organic layers were dried over sodium sulfate
7. concentrationconcentrated under vacuum

ORD record

ord-aff1664ff2a643f88bef5b4fcf6ce550

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085586B2