Triethylamine → 4-(4,4,4-Trifluorobutoxy)phenol

HRID 511718Notes

Reaction equation

HRID 511718 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]([F:22])([F:21])[F:20])=[CH:11][CH:10]=1)C1C=CC=CC=1.C(N(CC)CC)C>C1COCC1.[Pd]>[F:20][C:19]([F:21])([F:22])[CH2:18][CH2:17][CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 674558991-(Benzyloxy)-4-(4,4,4-trifluorobutoxy)benzene

Product 1

HCID 674549644-(4,4,4-Trifluorobutoxy)phenolYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

60 g (193 mmol) of 1-(benzyloxy)-4-(4,4,4-trifluorobutoxy)benzene, and 7.61 g of Pd/C are dissolved in 900 mL of THF. 5 mL of triethylamine are added to the suspension. The reaction is hydrogenated under atmospheric pressure for 2 hours. The suspension is filtrated of 400 g of hyflo. The organic phase is concentrated under reduced pressure. Filtration of the residue on 900 g silica gel using toluene:ethyl acetate 4:1 as eluent and concentration under reduced pressure yields 41 g of 4-(4,4,4-trifluorobutoxy)phenol as a reddish oil.

Workup

  1. filtrationThe suspension is filtrated of 400 g of hyflo
  2. concentrationThe organic phase is concentrated under reduced pressure
  3. filtrationFiltration of the residue on 900 g silica gel
  4. concentrationconcentration under reduced pressure

Sources & evidence

ORD record
ord-ef1aa17e29614c69bf6b09f8c1eaa6b5
Source dataset
uspto-grants-2015_08
Patent number
US09097938B2

Reaction notes

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