Acetone → Phenol, 4-(pentafluoroethyl)-

HRID 1913704Notes

Reaction equation

HRID 1913704 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-10ee132ff42043cf9e6f68da842998ce
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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