Water → 4-(2-Hydroxy-2-methyl-propoxy)benzonitrile

Temperature

80 °C

A mixture of 1-chloro-2-methyl-propan-2-ol (10 mL), 4-hydroxybenzonitrile (2.0 g, 16.8 mmol), potassium carbonate (9.3 g, 67.3 mmol), water (6 mL) and ethanol (60 mL) was heated at 80° C. overnight. The reaction mixture was cooled, concentrated in vacuo and residue was diluted with ether (200 mL) and filtered. The filtrate was washed with water (50 mL) and brine solution (50 mL). The organics were separated and dried over MgSO4 and 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. concentrationconcentrated in vacuo and residue
3. additionwas diluted with ether (200 mL)
4. filtrationfiltered
5. washThe filtrate was washed with water (50 mL) and brine solution (50 mL)
6. customThe organics were separated
7. dry with materialdried over MgSO4
8. custompurified by silica gel column chromatography

ORD record

ord-5d116b454f9a4d428593fff5a53f2942

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08828996B2