Dimethylformamide → 2-Propenoic acid, 2-methyl-, 2-[4-(chlorocarbonyl)phenoxy]ethyl ester

HRID 1033267Notes

Reaction equation

HRID 1033267 reaction equation
[C:1]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].CN(C)C=O.S(Cl)([Cl:26])=O>C1(C)C=CC=CC=1>[C:1]([O:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([Cl:26])=[O:15])=[CH:12][CH:11]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl Chloride2×HCID 155900104-(2-((2-Methyl-1-oxo-2-propen-1-yl)oxy)ethoxy)benzoic acid

Product 1

HCID 110867852-Propenoic acid, 2-methyl-, 2-[4-(chlorocarbonyl)phenoxy]ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

62.56 g of 4-methacryloyloxyethyloxybenzoic acid was charged to a flask with 0.5 g dimethyl formamide , and 54.38 ml of thionyl chloride was added dropwise under stirring. The reaction was exothermic. The reaction mixture was stirred overnight to give a clear brownish solution. The excess thionyl chloride was drawn off under vacuum. The residue was digested once with 20 ml of distilled toluene, and the toluene drawn off under vacuum. The residue was directly usable.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred overnight
  3. customto give a clear brownish solution

Sources & evidence

ORD record
ord-bc901076b4564fe8a5aa9e5ebdbbf39c
Source dataset
uspto-grants-1994_05
Patent number
US05310837

Reaction notes

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