Dimethylformamide → Methacryloyloxyacetyl chloride

HRID 1182638Notes

Reaction equation

HRID 1182638 reaction equation
[C:1]([O:6][CH2:7][C:8]([OH:10])=O)(=[O:5])[C:2]([CH3:4])=[CH2:3].CN(C)C=O.S(Cl)([Cl:18])=O>>[C:1]([O:6][CH2:7][C:8]([Cl:18])=[O:10])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 13060939[(2-Methylacryloyl)oxy]acetic acid

Product 1

HCID 20028045Methacryloyloxyacetyl chloride

Conditions

Temperature
70 °C

Procedure

Into a 100-mL reaction vessel with a condenser were added 30 g (purity: 46%, 95.1 mmol) of methacryloyloxyacetic acid (prepared in a method described in International Publication No. 96/41841 and the like), 347 mg (4.8 mmol/0.05 eq) of dimethylformamide and 47.6 g (380.5 mmol/4.0 eq) of thionyl chloride. The resulting solution was stirred at 70° C. for 1 hour and subjected to distillation purification, thereby obtaining 10.0 g of target methacryloyloxyacetyl chloride. The purity of the target product was 70%; and the yield of the target product was 45%.

Workup

  1. customInto a 100-mL reaction vessel with a condenser
  2. customprepared in a method
  3. distillationsubjected to distillation purification

Sources & evidence

ORD record
ord-eca517299a1443b98e6b4d17963aa625
Source dataset
uspto-grants-2014_03
Patent number
US08663897B2

Reaction notes

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