Ethyl Acetate → (4-(4-(Trifluoromethoxy)benzyl)phenyl)methanol

HRID 1496917Notes

Reaction equation

HRID 1496917 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]([F:28])([F:27])[O:9][C:10]1[CH:26]=[CH:25][C:13]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1.CCOC(C)=O>CCOCC>[F:7][C:8]([F:27])([F:28])[O:9][C:10]1[CH:26]=[CH:25][C:13]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 66707520Methyl 4-[4-(trifluoromethoxy)benzyl]benzoate

Product 1

HCID 66707469(4-(4-(Trifluoromethoxy)benzyl)phenyl)methanolYield 100.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LiAlH4 (55 mg, 1.45 mmol) was added to a solution of ester 94 (203 mg, 0.65 mmol) in ether (5 mL) and the mixture was stirred at room temperature for 3 h, then EtOAc (150 mL) was added. The organic layer was washed with water, the aqueous layer was re-extracted with EtOAc (100 mL), and the combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to give {4-[4-(trifluoromethoxy)benzyl]phenyl}methanol (95) (185 mg, quant.) as a white solid: mp (EtOAc/hexane) 60-61° C.; 1H NMR (CDCl3) δ 7.32-7.27 (m, 2H), 7.20-7.14 (m, 4H), 7.13-7.09 (m, 2H), 4.67 (s, 2H), 3.98 (s, 2H); HREIMS calcd for C15H13F3O2 m/z (M+) 282.0868, found 282.0866.

Workup

  1. washThe organic layer was washed with water
  2. extractionthe aqueous layer was re-extracted with EtOAc (100 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a06848ab4ea945d58713410c84816352
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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