4-Chlorobenzoyl chloride → HCID 14579767, compound

HRID 1607243Notes

Reaction equation

HRID 1607243 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-:11].[Al+3].[Cl-].[Cl-].[CH3:15][C:16]1[C:20]2[C:21]([OH:29])=[C:22]([CH2:26][CH2:27][CH3:28])[CH:23]=[C:24]([Cl:25])[C:19]=2[O:18][CH:17]=1>C(Cl)CCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:17]2[O:18][C:19]3[C:24]([Cl:25])=[CH:23][C:22]([CH2:26][CH2:27][CH3:28])=[C:21]([O:29][C:6](=[O:7])[C:5]4[CH:9]=[CH:10][C:2]([Cl:11])=[CH:3][CH:4]=4)[C:20]=3[C:16]=2[CH3:15])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14579737HCID 14579737, compound

Product 1

HCID 14579767HCID 14579767, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Procedure

A solution of p-chlorobenzoyl chloride (3.5 gm; 20mmoles) in ethylene dichloride (10 mL) was added slowly to a cooled suspension of aluminium chloride (5.36 gm; 40mmoles) in ethylene dichloride (200 mL). After stirring for a period of 15 minutes, 3-methyl 4-hydroxy-5-propyl-7-chlorobenzofuran (1.5 gm; 7mmoles) in ethylenedichloride (10 mL) was added over a period of 2 minutes. The reaction mixture was stirred at room temperature for 5 hours. It was cooled with an ice-bath and ice was added slowly. When the vigorous reaction subsided, the organic layer was separated and the agueous phase was extracted with methylene chloride. The organic phases were combined, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed on silica gel. Elution with 15% ethylacetate in hexane yielded 2.63 gm (75%) of 2-(p-chlorobenzoyl)-methyl-4-(p-chlorobenzoyloxy)-5-propyl-7-chlorobenzofuran, mp. 177°-182° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5 hours
  2. temperatureIt was cooled with an ice-bath
  3. additionice was added slowly
  4. customWhen the vigorous reaction
  5. customthe organic layer was separated
  6. extractionthe agueous phase was extracted with methylene chloride
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washElution with 15% ethylacetate in hexane

Sources & evidence

ORD record
ord-ddf38c01cd0a457c8864cb9d4d0758b5
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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