p-Anisoyl chloride → HCID 14579747, compound

HRID 1534234Notes

Reaction equation

HRID 1534234 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:16][C:17]1[C:21]2[C:22]([OH:30])=[C:23]([CH2:27][CH2:28][CH3:29])[CH:24]=[C:25]([F:26])[C:20]=2[O:19][CH:18]=1>C(Cl)CCl>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:1]([C:18]2[O:19][C:20]3[C:25]([F:26])=[CH:24][C:23]([CH2:27][CH2:28][CH3:29])=[C:22]([O:30][C:1](=[O:10])[C:2]4[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=4)[C:21]=3[C:17]=2[CH3:16])=[O:10])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14579736HCID 14579736, compound

Product 1

HCID 14579747HCID 14579747, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Procedure

A solution of p-anisoyl chloride (2.70 gm; 15.5 mmoles) in ethylene dichloride (10 mL) was added slowly to a cooled suspension of aluminium chloride (3.0 gm; 21.8 mmoles) in ethylene dichloride (100 mL). After stirring for a period of 10 minutes, 3-methyl-4-hydroxy-5-propyl-7-fluorobenzofuran (0.79 gm; 3.8 mmoles) in dichloroethylene (5 mL) was added over a period of 2 minutes. The reaction mixture was stirred at room temperature for 1 hour. It was cooled with an ice bath and ice was added slowly. When the vigorous reaction subsided, the organic layer was separated and the aqueous phase was extracted with methylene chloride. The organic phases were combined, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed on silica gel and eluted with 10% ethylacetate in hexane to yield 1.18 gm (63%) of 2-(p-methoxybenzoyl)-3-methyl-4-(p-methoxybenzoyloxy)-5-propyl-7-fluorobenzofuran.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 hour
  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 aqueous phase was extracted with methylene chloride
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washeluted with 10% ethylacetate in hexane

Sources & evidence

ORD record
ord-e44c33f2af9f4858b3673dd81454e088
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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