2-(3,4-Dichlorophenyl)-2-methylpropanal → 3-(3,4-Dichlorophenyl)-3-methylbutan-2-ol

HRID 83850Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:13])([CH3:12])[CH:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:14][Mg+].[Br-]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:13])([CH3:12])[CH:10]([OH:11])[CH3:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(3,4-dichlorophenyl)-2-methylpropanal (47.13 g, 0.217 mol) in Et2O (223 mL) at 0° C. was added a 3.0M solution of MeMgBr (217 mL, 0.651 mol) in Et2O. After stirring 2 h at 0° C., the reaction mixture was warmed to room temperature over 1 h. Then the reaction mixture was cooled to 0° C., quenched with H2O (100 mL) and 3N HCl (200 mL), extracted with EtOAc and washed with brine. The organic layer was dried over Na2SO4 and concentrated to afford the crude product, which was purified by column chromatography to yield 3-(3,4-dichlorophenyl)-3-methylbutan-2-ol (45.9 g, 90%). 1H NMR (400 MHz, CDCl3) δ 7.46 (d, 1H), 7.37 (d, 1H), 7.21 (dd, 1H), 3.83 (m, 1H), 1.31 (s, 3H), 1.29 (s, 3H), 1.05 (d, 3H).

Workup

temperaturethe reaction mixture was warmed to room temperature over 1 h
temperatureThen the reaction mixture was cooled to 0° C.
customquenched with H2O (100 mL) and 3N HCl (200 mL)
extractionextracted with EtOAc
washwashed with brine
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
customto afford the crude product, which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-8c21b2011cee45a5959486b1b45d757b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846739B2

Reaction notes

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