2-Hydroxy-4-(trifluoromethyl)benzoic acid → 2-Hydroxy-4-(trifluoromethyl)benzenemethanol

HRID 452440Notes

Reaction equation

HRID 452440 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[OH:5][CH2:4][C:3]1[CH:7]=[CH:8][C:9]([C:11]([F:13])([F:14])[F:12])=[CH:10][C:2]=1[OH:1]

Participants

3

Reactant 2

HCID 1645782-Hydroxy-4-(trifluoromethyl)benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 552555602-Hydroxy-4-(trifluoromethyl)benzenemethanolYield 54.6%

Procedure

To a solution of 2-hydroxy-4-(trifluoromethyl)benzoic acid (5.0 g, 24.3 mmol) in dry DEE (150 ml), under nitrogen atmosphere, lithium aluminium hydride (1.11 g, 29.2 mmol) was added in portions. The reaction mixture was stirred for 12 h at ambient temperature and then quenched with water and NaOH (5 M). Aqueous HCl (10%) was added and the aqueous phase was extracted with EtOAc. The combined organic phases were dried (Na2SO4), filtered and evaporated to dryness. The residue was purified by flash column chromatography (isooctane/EtOAc 1:1) to give the title compound (2.55 g). MS m/z (rel. intensity, 70 eV) 192 (M+, 32), 174 (45), 146 (bp), 145 (62), 96 (54).

Workup

  1. customquenched with water and NaOH (5 M)
  2. additionAqueous HCl (10%) was added
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash column chromatography (isooctane/EtOAc 1:1)

Sources & evidence

ORD record
ord-525c3e5bf55e43d79c7577a60d837085
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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