HCID 21252717, compound → 4-(3,3,3-Trifluoropropyl)phenol

HRID 1895712Notes

Reaction equation

HRID 1895712 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO.C1COCC1.C(Cl)Cl>[F:18][C:17]([F:19])([F:20])[CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1

Participants

6

Reactant 1

HCID 21252717HCID 21252717, compound

Product 1

HCID 134059054-(3,3,3-Trifluoropropyl)phenolYield 72.5%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-1-(benzyloxy)-4-(3,3,3-trifluoroprop-1-enyl)benzene (305 mg, 1.096 mmol) and palladium on carbon (305 mg, 10 wt. %, wet, Aldrich) in MeOH (15 mL) and THF (5 mL) was placed under hydrogen (1 Atm) for 4 hrs. The resulting mixture was diluted with CH2Cl2 and filtered through a pad of CELITE® 545 filter aid. The filtrate was evaporated under reduced pressure and then purified by flash chromatography on silica gel (0 to 30% EtOAc/hexanes) to yield the title compound (151 mg, 72%) as a colorless oil. MS (ESI) 189 (M−H).

Workup

  1. filtrationfiltered through a pad of CELITE® 545
  2. filtrationfilter aid
  3. customThe filtrate was evaporated under reduced pressure
  4. custompurified by flash chromatography on silica gel (0 to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8b56736dcff440ff864f4aa7da3a4506
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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