Water → (4'-(Trifluoromethyl)-[1,1'-biphenyl]-4-yl)methanol

HRID 530536Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]([F:25])([F:24])[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.O.[OH-].[K+]>C1COCC1>[F:7][C:8]([F:24])([F:25])[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:23]=[CH:22][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (2.0 M THF solution, 3.0 mL, 6.00 mmol) in dry THF (10 mL), commercially available 4-[4-(trifluoromethyl)-phenyl]-benzoic acid (0.4 g, 1.5 mmol) in dry THF (10 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.23 mL), 3.0 M KOH solution (0.23 mL) and H2O (0.77 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered, concentrated to dryness and the resulting crude product purified by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:EtOAc (from 100:0 to 70:30) to afford the title compound (0.3 g, 79%), as white solid. 1H NMR (DMSO-d6): δ 4.56 (d, J=5.7 Hz, 2H), 5.25 (t, J=5.7 Hz, 1H), 7.45 (d, J=8.1 Hz, 2H), 7.70 (d, J=8.1 Hz, 2H), 7.81 (d, J=8.1 Hz, 2H), 7.89 (d, J=8.1 Hz, 2H).

Workup

additionwas added dropwise
waitThe mixture was left
customto react at rt for 4 h
customat 0° C
filtrationfiltered
customto remove the solid residue
dry with materialthe organic phase dried over Na2SO4
filtrationThe organic solution was again filtered
concentrationconcentrated to dryness
customthe resulting crude product purified by column chromatography
washeluting with Cy

Sources & evidence

ORD record: ord-8190a69ee95849d2a2a2986f09f2adb3
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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