Carbon Disulfide → Methyl 5-[4-(3-chloropropanoyl)phenyl]pentanoate

HRID 1461493Notes

Reaction equation

HRID 1461493 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][C:21]([OH:23])=[O:22])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:24](=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][C:21]([O:23][CH3:24])=[O:22])=[CH:12][CH:13]=1)=[O:9]

Participants

5

Reactant 4

HCID 6348Carbon DisulfideHCID 16757Benzenepentanoic acidHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19980871Methyl 5-[4-(3-chloropropanoyl)phenyl]pentanoate

Procedure

In a stirring flask equipped with a reflux condenser are placed 9.3 g of AlCl3, 10 ml of CS2 and 1.98 ml of β-chloropropionyl chloride. To this mixture are added dropwise at room temperature within 5 minutes 3.61 g of 5-phenylvaleric acid (rinsing is carried out with 2 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 and 5.03 g of crystalline product are thus obtained.

Workup

  1. customIn a stirring flask equipped with a reflux condenser
  2. washrinsing
  3. temperaturewarmed slightly
  4. temperaturecooled
  5. additionThe reaction mixture is then pipetted into a stirred mixture of ice, water and ether
  6. washThe organic phase is washed neutral with bicarbonate solution and water
  7. dry with materialAfter drying over MgSO4 the solvent
  8. customis removed

Sources & evidence

ORD record
ord-05c008ea080c4cd999319d4769c3f80b
Source dataset
uspto-grants-1991_12
Patent number
US05075447

Reaction notes

Loading…