Acetic Acid → 3-Acetyl-3-phenylfuran

HRID 486555Notes

Reaction equation

HRID 486555 reaction equation
[C:1]1([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](O)(=[O:14])[CH3:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)C>[C:12]([C:10]1[O:9][CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=1)(=[O:14])[CH3:13].[C:12]([C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:11]=[CH:10][O:9][CH2:8]1)(=[O:14])[CH3:13]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 5188023-Phenylfuran

Product 2

HCID 190953503-Acetyl-3-phenylfuranYield 43%HCID 190954162-Acetyl-4-phenylfuranYield 13%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

3-Phenylfuran (4.3 g) was dissolved in 80 ml of acetonitrile under argon and treated while stirring with 8.6 g of the mixed anhydride from acetic acid and p-toluenesulphonic acid. The reaction solution was stirred at room temperature for 64 hours and subsequently stirred with 150 ml of saturated sodium hydrogen carbonate solution and 150 ml of diethyl ether 30 minutes. The phases were separated and the aqueous phase was extracted once with a further 100 ml of diethyl ether. The organic phases were combined, washed with 100 ml of water, dried over MgSO4 and freed from solvent. The residue was chromatographed on 200 g of silica gel with methylene chloride/hexane (1:1) as the eluent. There was obtained 0.7 g (13%) of 2-acetyl-4-phenylfuran besides 2.4 g (43%) of 3-acetyl-3-phenylfuran. The former was processed without further purification.

Workup

  1. additiontreated
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted once with a further 100 ml of diethyl ether
  4. washwashed with 100 ml of water
  5. dry with materialdried over MgSO4
  6. customThe residue was chromatographed on 200 g of silica gel with methylene chloride/hexane (1:1) as the eluent

Sources & evidence

ORD record
ord-8ef7e02077ef485fa784be232c746b00
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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