Benzene → HCID 15096993, compound

HRID 846731Notes

Reaction equation

HRID 846731 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1.[CH3:26][C:27](=[O:30])[CH:28]=[CH2:29]>O(CC)CC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:29][CH2:28][C:27](=[O:30])[CH3:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 6570Methyl vinyl ketoneHCID 97324-Fluorophenol

Product 1

HCID 15096993HCID 15096993, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 134 parts of 4-fluorophenol and 2 parts of 4-methylbenzenesulfonic acid in 1080 parts of benzene were added 42 parts of 3-buten-2-one. Stirring was continued for 4 days at room temperature. 700 Parts of 1,1'-oxybisethane were added and the whole was washed four times with 500 parts of a cold sodium hydroxide solution 1N and with water. The organic phase was dried, filtered and evaporated. The oily residue was purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The oily residue solidified upon cooling. The product was suspended in cold petroleumether. The product was filtered off and dried at room temperature, yielding 43.4 parts (39.7%) of 4-(4-fluorophenoxy)-2-butanone (intermediate 26).

Workup

  1. washthe whole was washed four times with 500 parts of a cold sodium hydroxide solution 1N
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe oily residue was purified by column-chromatography over silica gel
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. temperatureupon cooling
  9. filtrationThe product was filtered off
  10. customdried at room temperature

Sources & evidence

ORD record
ord-5a7dfc871f6f4a8a91f229fc63aff1ed
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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