Toluene → 4-Acetoxypentanoic acid chloride

HRID 487500Notes

Reaction equation

HRID 487500 reaction equation
[C:1]([O:4][CH:5]([CH3:11])[CH2:6][CH2:7][C:8](O)=[O:9])(=[O:3])[CH3:2].C1(C)C=CC=CC=1.C(Cl)(=O)C([Cl:22])=O>CN(C)C=O>[C:1]([O:4][CH:5]([CH3:11])[CH2:6][CH2:7][C:8]([Cl:22])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 147371984-Acetoxypentanoic acid

Product 1

HCID 543443094-Acetoxypentanoic acid chlorideYield 81.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

46.5 g (0.29 mol) of 4-acetoxypentanoic acid are dissolved at room temperature in 230 ml of abs. toluene, and then 0.2 ml of abs. Dimethyl formamide is added. Then 32.6 ml (0.38 mol) of oxalyl chloride are added dropwise such that the evolution of gas remains under control. When the dropwise addition is complete, the reaction mixture is heated to 50° C. and stirred for 1 hour at this temperature. The orange-red reaction solution is concentrated by evaporation. Distillation of the residue gives 42.2 g of 4-acetoxypentanoic acid chloride as a colorless liquid of b.p.34 110°-112° C.

Workup

  1. additionWhen the dropwise addition
  2. concentrationThe orange-red reaction solution is concentrated by evaporation
  3. distillationDistillation of the residue

Sources & evidence

ORD record
ord-4ae95b053e4641799505f83a8fb9265b
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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