Toluene → 4-Ethoxycarbonylmethoxybutyric acid chloride

HRID 487491Notes

Reaction equation

HRID 487491 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:5])[CH3:2].C1(C)C=CC=CC=1.C(Cl)(=O)C([Cl:24])=O>CN(C)C=O>[CH2:1]([O:3][C:4]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][C:11]([Cl:24])=[O:13])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 223185004-Ethoxycarbonylmethoxybutyric acid

Product 1

HCID 543801394-Ethoxycarbonylmethoxybutyric acid chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

36 g (0.19 mol) of 4-ethoxycarbonylmethoxybutyric acid are charged to 180 ml of toluene and 0.1 ml of dimethyl formamide is added. Then 24.4 ml (0.28 mol) of oxalyl chloride are added dropwise over 30 minutes. When the addition is complete, the reaction mixture is heated to 50° C., stirred for 1 hour and concentrated by evaporation. Distillation of the residue gives 4-ethoxycarbonylmethoxybutyric acid chloride as a clear colourless liquid of b.p. 87°-89° C./2.10-2 torr.

Workup

  1. additionis added
  2. additionWhen the addition
  3. concentrationconcentrated by evaporation
  4. distillationDistillation of the residue

Sources & evidence

ORD record
ord-d3a0c92a93c04f968a9d7f48ee15fbac
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

Loading…