p-Anisoyl chloride → HCID 14579748, compound

HRID 1607262Notes

Reaction equation

HRID 1607262 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]([Cl: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]([Cl: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 14579737HCID 14579737, compound

Product 1

HCID 14579748HCID 14579748, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Procedure

A solution of p-anisoyl chloride (3.5 gm; 20.5mmoles) in ethylene dichloride (10 mL) was added slowly to a cooled suspension of aluminium chloride (4.0 gm; 30mmoles) in ethylene dichloride (100 mL). After stirring for a period of 10 minutes, 3-methyl-4-hydroxy-5-propyl-7-chlorobenzofuran (1.14 gm; 5 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 separatd 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 and eluted with 10% ethylacetate in hexane to yield 1.92 gm (78%) of 2-(p-methoxybenzoyl)-3-methyl-4-(p-methoxybenzoyloxy)5-propyl-7-chlorobenzofuran, mp.103°-105° C.

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. extractionthe agueous phase was extracted with methylene chloride
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel
  9. washeluted with 10% ethylacetate in hexane

Sources & evidence

ORD record
ord-ef1b107212f44ac89c986e92675baef1
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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