3-Chloropropionyl chloride → HCID 19980875, compound

HRID 1252669Notes

Reaction equation

HRID 1252669 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][C:8](Cl)=[O:9].[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(=S)=S>[Cl:5][CH2:6][CH2:7][C:8]([C:14]1[CH:15]=[CH:16][C:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:12][CH:13]=1)=[O:9]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 118203006-phenyl-hexanoic acid methyl ester

Product 1

HCID 19980875HCID 19980875, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

17.2 g of AlCl3, 18.5 ml of CS2 and 3.6 ml of β-chloro-propionyl chloride are placed in a stirring flask with a reflux condenser. 7.06 g of methyl 6-phenylcaproate are allowed to drop into this mixture at room temperature within 10 minutes (rinsing is carried out with 4 ml of CS2). The reaction mixture is subsequently stirred for a further 15 minutes, warmed slightly and then cooled. The reaction mixture is then pipetted into a stirred mixture of ice, water and ether. The organic phase is washed neutral with bicarbonate solution and water. After drying over MgSO4 the solvent is removed, 10.2 g of crystalline product identified as methyl p-[β-chloropropionyl]-6-phenyl-caproate are obtained.

Workup

  1. wash(rinsing
  2. temperaturewarmed slightly
  3. temperaturecooled
  4. additionThe reaction mixture is then pipetted into a stirred mixture of ice, water and ether
  5. washThe organic phase is washed neutral with bicarbonate solution and water
  6. dry with materialAfter drying over MgSO4 the solvent
  7. customis removed
  8. customare obtained

Sources & evidence

ORD record
ord-c766bea08f37448d9ad563453645e942
Source dataset
uspto-grants-1988_05
Patent number
US04745076

Reaction notes

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