Acetyl chloride → Ethyl 5-(4-acetylphenyl)benzofuran-2-carboxylate

HRID 2057971Notes

Reaction equation

HRID 2057971 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]1([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:15]=3[CH:24]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[C:1]([C:8]1[CH:9]=[CH:10][C:5]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:15]=3[CH:24]=2)=[CH:6][CH:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 20329644Ethyl 5-phenylbenzofuran-2-carboxylate

Product 1

HCID 20329647Ethyl 5-(4-acetylphenyl)benzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

12.2 g of acetyl chloride was added to a mixture of 10.3 g of 1B, and 120 ml of carbon disulfide, then 21.8 g of anhydrous aluminum chloride was added in portions to the stirred mixture. The mixture then was stirred at room temperature for 2.5 hours, the temperature rising to 32° C. The mixture was poured into 1 liter of ice water, and stirred for 30 minutes, and the solution was extracted with ether. The extract was dried (MgSO4) and concentrated. The residue was washed with ether and dissolved in 100 ml of chloroform. The solution was treated with activated charcoal, and 100 ml of hexane was added. The resulting solution was concentrated to about 100 ml and cooled to give ethyl 5-(4-acetylphenyl)-benzofuran-2-carboxylate (10A), mp: 105°-107° l C.

Workup

  1. customrising to 32° C
  2. stirringstirred for 30 minutes
  3. extractionthe solution was extracted with ether
  4. dry with materialThe extract was dried (MgSO4)
  5. concentrationconcentrated
  6. washThe residue was washed with ether
  7. dissolutiondissolved in 100 ml of chloroform
  8. additionThe solution was treated with activated charcoal, and 100 ml of hexane
  9. additionwas added
  10. concentrationThe resulting solution was concentrated to about 100 ml
  11. temperaturecooled

Sources & evidence

ORD record
ord-388b0c76af53454abbf607bce23e84b3
Source dataset
uspto-grants-1980_07
Patent number
US04213998

Reaction notes

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