O-Xylene → HCID 54487403, compound

HRID 893908Notes

Reaction equation

HRID 893908 reaction equation
[Cl-:1].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:28](=O)[C:29]1[O:33][CH:32]=[CH:31][CH:30]=1.C1(C)C(C)=CC=CC=1>C(OCC)(=O)C>[O:33]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH:28]=[CH:8][C:3](=[O:2])[CH2:4][CH2:5][CH2:6][CH2:7][Cl:1]

Participants

5

Reactant 3

HCID 7237O-Xylene2×HCID 7362FurfuralHCID 73680070[(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium chloride

Product 1

HCID 54487403HCID 54487403, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2 parts of [(tetrahydro-2H-pyran-2-ylidene)methyl] triphenylphosphonium chloride and 1 part of furfural were combined in 45 parts of xylene. This was maintained under a nitrogen atmosphere and was refluxed for about 24 hours to give a black solution. After cooling the reaction mixture to room temperature xylene was removed from this solution at a temperature of about 40°-60° C. under reduced pressure, leaving a product mixture. This mixture was seprated chromatographically on a silica column using as the elution solvent a solution of 20 percent by volume of ethyl acetate in Skelly B, to yield 1-(2-furyl)7-chloro-1-hepten-3-one which, after a recrystallization from n-pentane, melted at about 50°-52° C.

Workup

  1. temperatureThis was maintained under a nitrogen atmosphere
  2. temperaturewas refluxed for about 24 hours
  3. customto give a black solution
  4. customwas removed from this solution at a temperature of about 40°-60° C. under reduced pressure
  5. customleaving a product mixture

Sources & evidence

ORD record
ord-d42883f314bb44198971687a519ec190
Source dataset
uspto-grants-1981_08
Patent number
US04282158

Reaction notes

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