Potassium Carbonate → 4-(2-Hydroxy-2-methyl-propoxy)benzonitrile

Temperature

80 °C

A mixture of 1-chloro-2-methyl-propan-2-ol (10 mL), 4-hydroxybenzonitrile (2 g, 16.8 mmol), K2CO3 (9.3 g, 67.3 mmol) in water (6 mL) and ethanol (60 mL) was heated at 80° C. for 16 hours. The reaction mixture was cooled and the solvent was concentrated in vacuo. The residue was diluted with ether (200 mL) and filtered and the filtrate was washed sequentially with water (50 mL) and brine solution (50 mL). The organics were separated and dried over MgSO4 and solvent was removed in vacuo to give a residue which was purified by silica gel column chromatography using (0-100%) EtOAc/DCM as eluent to give 4-(2-hydroxy-2-methyl-propoxy)benzonitrile (3.0 g, 94%) as a yellow solid. ESI-MS m/z calc. 191.1. Found 192.3 (M+1)+; Retention time: 1.05 minutes (3 min run).

1. temperatureThe reaction mixture was cooled
2. concentrationthe solvent was concentrated in vacuo
3. additionThe residue was diluted with ether (200 mL)
4. filtrationfiltered
5. washthe filtrate was washed sequentially with water (50 mL) and brine solution (50 mL)
6. customThe organics were separated
7. dry with materialdried over MgSO4 and solvent
8. customwas removed in vacuo
9. customto give a residue which
10. customwas purified by silica gel column chromatography

ORD record

ord-40f4c4f2187f4862a629eb352e98726d

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828996B2