3-Chloropropionyl chloride → HCID 19980875, compound

HRID 1461494Notes

Reaction equation

HRID 1461494 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-edf8e4fb6ef146b79ed77c1bbc79d612
Source dataset
uspto-grants-1991_12
Patent number
US05075447

Reaction notes

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