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

HRID 277176Notes

Reaction equation

HRID 277176 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 2,5-difluorophenol allyl ether was dissolved in 90 ml N,N-dimethylaniline and stirred at 170° C. for 5 hours in a nitrogen stream. The reaction solution was poured into 10% aqueous hydrogen chloride solution and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then evaporated The resulting residue was subjected to silica gel chromatography (developing solvent: 7% ethyl acetate/n-hexane) to give 7.8 g of 2-allyl-3,6-difluorophenol as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated The resulting residue

Sources & evidence

ORD record
ord-5721013ff3da4700b2908d8de6d458df
Source dataset
uspto-grants-2002_03
Patent number
US06355669B1

Reaction notes

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