Acetone → Phenol, 4-(pentafluoroethyl)-

HRID 2190818Notes

Reaction equation

HRID 2190818 reaction equation
C(OC[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1)C.CC(C)=O.Cl>O>[F:17][C:12]([F:18])([C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=1)[C:13]([F:14])([F:16])[F:15]

Participants

5

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 866510611-Ethoxymethoxy-4-pentafluoroethyl benzene

Product 1

HCID 10856782Phenol, 4-(pentafluoroethyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

7.39 g of 1-ethoxymethoxy-4-pentafluoroethyl benzene, 30 ml of acetone and 30 ml of 6 M hydrochloric acid were stirred while heating at 50° C. for 2.5 hours. The reaction mixture was cooled to room temperature, and then poured into water, followed by extraction with ethyl acetate. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 4-(pentafluoroethyl)phenol.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b22f804897764aeaa1eca51c544b7ccd
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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