Aluminium lithium hydride → (4-Isopropoxy-3-(trifluoromethyl)phenyl)methanol

HRID 1964119Notes

Reaction equation

[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O-])=[O:10])=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(Cl)Cl>[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[C:14]([F:15])([F:16])[F:17])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (−78° C.) solution of 4-isopropoxy-3-(trifluoromethyl)benzoate (13.1 mmol) in DCM (85 mL) under nitrogen was added 2.0 M solution of LAH (19.0 mmol) by a syringe. The reaction was allowed to return to room temperature and stirred for 16 h. The reaction was cooled to 0° C. and quenched with water (0.95 mL) and 10% NaOH (aq) (1.90 mL). The mixture was filtered through Celite®. The filtrate was concentrated under vacuum to give the title compound as an oil (11.27 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.27 (d, J=6.06 Hz, 6H), 4.46 (d, J=5.81 Hz, 2H), 4.75 (septet, J=6.02 Hz, 1H), 5.20 (t, J=5.75 Hz, 1H), 7.23 (d, J=8.46 Hz, 1H), 7.47-7.56 (m, 2H).

Workup

customto return to room temperature
customquenched with water (0.95 mL) and 10% NaOH (aq) (1.90 mL)
filtrationThe mixture was filtered through Celite®
concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record: ord-e619eedb033c484d92f0b2af35788697
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415484B2

Reaction notes

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