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

HRID 2291605Notes

Reaction equation

HRID 2291605 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

At room temperature, 8.0 g of anhydrous aluminum chloride and 3.59 g of itaconic acid anhydride were dissolved in distilled tetrachloroethane, 20 ml, with vigorous agitation. Then the solution was cooled on an ice-water bath and to this, 2-ethybenzofuran, 4.39 g, dissolved in 10 ml of tetrachloroethane were added dropwise. After three hours stirring in an ice-water bath followed by 12 hrs. stirring at room temperature, the reaction mixture was poured into ice-water, 80 g, containing 20 ml of HCl and extracted with ethyl acetate. The ethyl acetate layer was extracted with 50 ml of a 10% NaCO3 solution and then the aqueous layer was acidified with 10% HCl again and extracted with ethyl acetate. After washing with water, drying and removal of the solvent, the resulting viscous oily substance was extracted with ligroin (20 ml×3). Needle-like crystals were obtained after overnight standing at room temperature.

Workup

  1. temperatureThen the solution was cooled on an ice-water bath
  2. additionwere added dropwise
  3. waitfollowed by 12 hrs
  4. stirringstirring at room temperature
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate layer was extracted with 50 ml of a 10% NaCO3 solution
  7. extractionextracted with ethyl acetate
  8. washAfter washing with water
  9. customdrying
  10. customremoval of the solvent
  11. extractionthe resulting viscous oily substance was extracted with ligroin (20 ml×3)
  12. customNeedle-like crystals were obtained after overnight
  13. customstanding at room temperature

Sources & evidence

ORD record
ord-59e2747a41f042ff9cf8ca49a4d7adf7
Source dataset
uspto-grants-1989_01
Patent number
US04797415

Reaction notes

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