Toluene → 4-Ethoxycarbonylmethoxybutyric acid chloride

HRID 376157Notes

Reaction equation

HRID 376157 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-ethoxycarbonyhnethoxybutyric 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-febb8b92ed0c431aa2694ccef7394467
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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