4-(2-Hydroxypropan-2-yl)benzonitrile → 2-[4-(Aminomethyl)phenyl]propan-2-ol

Temperature

0 °C

To a stirred solution of 4-(1-hydroxy-1-methyl-ethyl)-benzonitrile (20.9 g, 0.13 mol.) in dry tetrahydrofuran (300 mL) at 0° C. was added slowly dropwise 1.0M lithium aluminium hydride in tetrahydrofuran (388 mL, 0.39 mol.). The mixture was refluxed for 30 min. then cooled to 0° C. and quenched with methanol (50 mL) added slowly dropwise. The mixture was concentrated in vacuo to half volume and diluted with chloroform (1200 mL) then washed with water (300 mL). The resulting suspension was filtered through Celite and the filtrate layers seperated. The organic extract was dried (MgSO4) and concentrated to give 16.2 g as a light yellow solid mp 64-6° C. NMR (CDCl3): 7.45 (d, 2H), 7.26 (d, 2H), 3.83 (s, 2H), 1.57 (s, 6H). GC-MS (m/e, %): 164 (M+, 15), 150 (80), 132 (75), 106 (100).

1. temperatureThe mixture was refluxed for 30 min.
2. customquenched with methanol (50 mL)
3. additionadded slowly dropwise
4. concentrationThe mixture was concentrated in vacuo to half volume
5. additiondiluted with chloroform (1200 mL)
6. washthen washed with water (300 mL)
7. filtrationThe resulting suspension was filtered through Celite
8. customthe filtrate layers seperated
9. extractionThe organic extract
10. dry with materialwas dried (MgSO4)
11. concentrationconcentrated

ORD record

ord-bdb124c77c67416583e7dc0923ec109a

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06380218B1