Acetyl chloride → Methyl 3-acetyl-2-methylbenzofuran-7-carboxylate

HRID 1761934Notes

Reaction equation

HRID 1761934 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[CH:6]=1.[C:15](Cl)(=[O:17])[CH3:16].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[C:15]([C:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[C:4]=2[O:3][C:2]=1[CH3:1])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 14229729Methyl 2-methyl-1-benzofuran-7-carboxylate

Product 1

HCID 14229733Methyl 3-acetyl-2-methylbenzofuran-7-carboxylateYield 88.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 1.0 g of methyl 2-methylbenzofuran-7-carboxylate, 1.24 g of acetyl chloride, 2.15 g of aluminum chloride and 20 ml of dichloroethane is heated at 50°-60° C. for 1 hour. The reaction mixture is poured into ice-water and the aqueous mixture is extracted with chloroform. The extract is washed with water, dried and evaporated to remove solvent. The residue is recrystallized from ethyl acetate-n-hexane to give 1.08 g of methyl 3-acetyl-2-methylbenzofuran-7-carboxylate as colorless needles.

Workup

  1. temperatureis heated at 50°-60° C. for 1 hour
  2. extractionthe aqueous mixture is extracted with chloroform
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-f6323838053e448f9fcde35dcc226a4c
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

Loading…