Hydrochloric Acid → HCID 21425053, compound

HRID 258886Notes

Reaction equation

HRID 258886 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]([CH2:9][CH2:10][C:11](Cl)=[O:12])([O:7][CH3:8])=[O:6].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.Cl>ClCCCl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:25][C:24]([C:11](=[O:12])[CH2:10][CH2:9][C:5]([O:7][CH3:8])=[O:6])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 6451240Aluminum(III) ChlorideHCID 10965101HCID 10965101, compound

Product 1

HCID 21425053HCID 21425053, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a stirring mixture of 62 g (0.50 mole) of AlCl3 in 375 ml of 1,2-dichloroethane was added portionwise 75 g (0.5 mole) of 3-carbomethoxypropionyl chloride while keeping the temperature below 25° by means of an ice bath. The reaction mixture was cooled to 15° and a solution of 89 g (0.5 mole) of 5-(4-chlorophenyl)furan in 250 ml of 1,2-dichloroethane was added dropwise with HCl gas being evolved and the temperature rising to 30°. The reaction mixture was stirred at ambient temperature for 1 hour and then added to 1000 ml of ice/water. The organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with 1000 ml of 6% sodium carbonate solution with 1000 ml of water and dried over MgSO4. The solvent was removed on a Calab evaporator yielding a residual oil which was extracted several times with refluxing hexane. The hexane extracts were cooled to yield a solid which was filtered, washed twice with 6% sodium carbonate solution, recrystallized from hexane and air dried to yield 7 g (5%). An analytical sample was prepared by drying a sample in a vacuum pistol at room temperature, m.p. 99°-100°.

Workup

  1. customthe temperature below 25°
  2. temperatureThe reaction mixture was cooled to 15°
  3. customrising to 30°
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted with dichloromethane
  6. washThe combined organic layers were washed with 1000 ml of 6% sodium carbonate solution with 1000 ml of water
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed on a Calab evaporator
  9. customyielding a residual oil which
  10. extractionwas extracted several times with refluxing hexane
  11. temperatureThe hexane extracts were cooled
  12. customto yield a solid which
  13. filtrationwas filtered
  14. washwashed twice with 6% sodium carbonate solution
  15. customrecrystallized from hexane and air
  16. customdried
  17. customto yield 7 g (5%)
  18. customAn analytical sample was prepared
  19. customby drying a sample in a vacuum pistol at room temperature

Sources & evidence

ORD record
ord-0b611653feb542e18778802b9b2e3c78
Source dataset
uspto-grants-1977_07
Patent number
US04035394

Reaction notes

Loading…