2-Phenyl-2-propanol → HCID 68997673, compound

Temperature

60 °C

To a solution of 4-chloro-3-nitrophenol (0.5 g), tri(n-butyl)phosphine (0.72 mL) and 2-phenyl-2-propanol (0.26 g) in tetrahydrofuran (5 mL) was added 1, 1′-azobis (N,N-dimethyl -formamide) (0.5 g), and the mixture was stirred at 60° C. for 20 hours. The reaction mixture was diluted with diethyl ether, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=10/1) to give 2-chloro-5-(1-methyl-1-phenylethoxy)-1-nitrobenzene (0.19 g). This material was dissolved in tetrahydrofuran (3.5 mL). To the solution were added methanol (3.5 mL), nickel(II) bromide (11 mg) and sodium borohydride (0.12 g) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. Then the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate =3/1) to give the title compound (0.14 g).

1. customthe insoluble material was removed by filtration
2. concentrationThe filtrate was concentrated under reduced pressure
3. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=10/1)

ORD record

ord-ca225e1e82554f40a87a61cc4dd8d8d6

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040693B2