Toluene → 4-Acetoxypentanoic acid chloride

HRID 376166Notes

Reaction equation

HRID 376166 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 colourless 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-f07c916ccf964837ade5afd1f6aa4503
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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