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

HRID 1395682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1395682
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel

Versuchsvorschrift

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, the mixture was 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 dried. It was dissolved in 100 ml of chloroform, the solution was treated with a decolorizing agent, 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 (6A), mp: 105°-107° C.

Aufarbeitung

  1. customrising to 32° C
  2. stirringthe mixture was stirred 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. customdried
  8. dissolutionIt was dissolved in 100 ml of chloroform
  9. additionthe solution was treated with a decolorizing agent, and 100 ml of hexane
  10. additionwas added
  11. concentrationThe resulting solution was concentrated to about 100 ml
  12. temperaturecooled

Quellen und Nachweise

ORD-Eintrag
ord-275c3d4a156743349e28d68cbbc739c0
Quelldatensatz
uspto-grants-1980_05
Patentnummer
US04205080

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