Hydrochloric Acid → HCID 21425053, compound

HRID 437406Notes

Reaction equation

HRID 437406 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-dichlorethane 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-chlorphenyl)furan in 250 ml of 1,2-dichloroethane was added dropwise with large volumes of HCl gas being evolved and the temperature rising to 30°. The reaction mixture was stirred at ambient temperature for one hour and then added to 1000 ml of ice water. The organic layer was separated and the aqueous layer extracted with dichlormethane. 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 the 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 dichlormethane
  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 the 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-fd79acadbf104ec5b9ff69cfd632fa89
Source dataset
uspto-grants-1977_06
Patent number
US04031113

Reaction notes

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