Hydrochloric Acid → 2-Allyl-3,6-difluorophenol

HRID 278053Notes

Reaction equation

HRID 278053 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[F:12])C=C.Cl.CN(C)[C:16]1[CH:21]=CC=C[CH:17]=1>>[CH2:21]([C:10]1[C:9]([F:11])=[CH:8][CH:7]=[C:6]([F:12])[C:5]=1[OH:4])[CH:16]=[CH2:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 107496562,5-Difluorophenol allyl ether

Product 1

HCID 108448632-Allyl-3,6-difluorophenol

Conditions

Temperature
170 °C

Procedure

13 g of 2,5-difluorophenol allyl ether was dissolved in 90 ml of N,N-dimethylaniline. The resulting solution was stirred at 170° C. under nitrogen stream for 5 hours and poured into a 10% aqueous solution of hydrogen chloride. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated. The resutling residue was subjected to silica gel chromatography (developer: 7% ethyl acetate/n-hexane) to give 7.8 g of the title compound as a colorless oil.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-d75139a7d514496690787d258b734b51
Source dataset
uspto-grants-2002_03
Patent number
US06358995B1

Reaction notes

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