Hydrogen Peroxide → 4-(2-Fluoroethoxy)phenol

HRID 1583586Notes

Reaction equation

HRID 1583586 reaction equation
C[OH:2].S(=O)(=O)(O)O.[F:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15](C(C)=C)=[CH:14][CH:13]=1.OO>O>[F:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:2])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 1118Sulfuric AcidHCID 202592654-(2-Fluoroethoxy)isopropenylbenzene

Product 1

HCID 150586584-(2-Fluoroethoxy)phenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Then, a mixture of 30 ml of methanol and 2 ml of concentrated sulfuric acid was warmed to 40° C., and 9.0 g of the resulting crude 4-(2-fluoroethoxy)-isopropenylbenzene prepared as above and a 30% aqueous solution of hydrogen peroxide were separately added dropwise to the warmed mixture over the course of 20 minutes. The reaction was continued for 1 hour. The reaction mixture was cooled, poured into water, and extracted with toluene. The toluene layer was washed with water, and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure to give 7.3 g of crude 4-(2-fluoroethoxy)phenol. The resulting crude phenol was recrystallized to give 6.8 g of pure 4-(2-fluoroethoxy)phenol as crystals.

Workup

  1. additionwere separately added dropwise to the warmed mixture over the course of 20 minutes
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with toluene
  4. washThe toluene layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customToluene was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1f55a6682b5147af894f6a56cda6064a
Source dataset
uspto-grants-1985_11
Patent number
US04552894

Reaction notes

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