Hydrochloric Acid → 2-Methylene-4-oxo-4-(2-ethyl-3-benzofuranyl)butyric acid

HRID 1681949Notes

Reaction equation

HRID 1681949 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:12])[O:11][C:9](=[O:10])[CH2:8][C:6]1=[CH2:7].[CH2:13]([C:15]1[O:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[CH:19]=1)[CH3:14].Cl>ClCC(Cl)(Cl)Cl>[CH2:7]=[C:6]([CH2:8][C:9](=[O:10])[C:19]1[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][C:15]=1[CH2:13][CH3:14])[C:5]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 75110Itaconic AnhydrideHCID 765822-EthylbenzofuranHCID 6451240Aluminum(III) Chloride

Product 1

HCID 143701302-Methylene-4-oxo-4-(2-ethyl-3-benzofuranyl)butyric acid

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent2×

Procedure

A suspension of 8.0 g of anhydrous aluminum chloride and 3.59 g of itaconic acid anhydride in dried tetrachloroethane was stirred for one hour at room temperature. To this solution, 4.39 g of 2-ethylbenzofuran dissolved in 10 ml of tetrachloroethane was added dropwise under cooling by ice-water. And then stirring was continued for 3 hrs. in ice-water and for 12 hrs. at room temperature. The reaction mixture was poured into the mixture of 80 g of ice and 20 ml of conc. HCl, then extracted with ethylacetate (50 ml). After washed with water, the solvent layer was made alkaline with 10% NaCO3 solution. The water layer was acidified with 10% HCl again and then was extracted with ethylacetate. The brown viscous residue obtained after washing, drying and removal of ethyl acetate layer, was extracted with ligroin. After standing overnight, the needle-like crystals were obtained.

Workup

  1. additionwas added dropwise
  2. stirringAnd then stirring
  3. waitwas continued for 3 hrs
  4. customat room temperature
  5. extractionextracted with ethylacetate (50 ml)
  6. washAfter washed with water
  7. extractionwas extracted with ethylacetate
  8. customThe brown viscous residue obtained
  9. washafter washing
  10. customdrying
  11. customremoval of ethyl acetate layer
  12. extractionwas extracted with ligroin
  13. waitAfter standing overnight
  14. customthe needle-like crystals were obtained

Sources & evidence

ORD record
ord-00f2a15ec8cb4bb4ac95ee1adeb5bca2
Source dataset
uspto-grants-1992_12
Patent number
US05175184

Reaction notes

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