Carbon Tetrachloride → HCID 20509989, compound

HRID 1758266Notes

Reaction equation

HRID 1758266 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[CH3:25][C:26]1[CH:35]=[CH:34][C:29]2C(=O)[CH2:31][O:32][C:28]=2[CH:27]=1>C1(C)C=CC=CC=1>[Cl:24][C:20]1[C:29]2[CH:34]=[CH:35][C:26]([CH3:25])=[CH:27][C:28]=2[O:32][CH:31]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 303496-Methyl-1-benzofuran-3(2H)-one

Product 1

HCID 20509989HCID 20509989, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of triphenylphosphine (8.8 g, 0.033 mol) and carbon tetrachloride (19.5 cm3) was stirred at 60° C. for 2 hr. A solution of 6-methylbenzofuran-3(2H)-one (5.0 g, 0.034 mol) in toluene (50 cm3) was added dropwise and the mixture was stirred at 115° C. for 18 hr. The cooled mixture was filtered and the solvent was removed from the filtrate. The residue was extracted with hot petroleum ether (b.p. 60°-80° C.). The extract was chromatographed on silica using petroleum ether (b.p. 60°-80° C.) as the eluant to give 3-chloro-6-methylbenzofuran (2.3 g, 0.014 mol, 40.0%) RF 0.51.

Workup

  1. stirringthe mixture was stirred at 115° C. for 18 hr
  2. filtrationThe cooled mixture was filtered
  3. customthe solvent was removed from the filtrate
  4. extractionThe residue was extracted with hot petroleum ether (b.p. 60°-80° C.)
  5. customThe extract was chromatographed on silica

Sources & evidence

ORD record
ord-616dc12a9a1b494bba2c44a34662c6e2
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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