Dimethylformamide → 4-methacryloyloxybutyl (E)-3-(4-ethoxycarbonyloxyphenyl)acrylate

HRID 1637133Notes

Reaction equation

HRID 1637133 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:17]=[CH:16][C:10](/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:9][CH:8]=1)=[O:5])[CH3:2].CN(C)[CH:20]=[O:21]>S(Cl)(Cl)=O>[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:17]=[CH:16][C:10](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:10][CH2:9][CH2:8][CH2:7][O:6][C:20](=[O:21])[C:12]([CH3:13])=[CH2:11])=[O:14])=[CH:9][CH:8]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 12876666(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acid

Product 1

HCID 220777024-methacryloyloxybutyl (E)-3-(4-ethoxycarbonyloxyphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5.2 g of 4-(E)-ethyloxycarbonyloxycinnamic acid in 20 ml of thionyl chloride and 0.05 ml of N,N-dimethylformamide was heated under reflux for 3 hours. Subsequently, excess thionyl chloride was distilled off. 3.3 g of 4-hydroxybutyl methacrylate were added dropwise to a solution of the resulting 4-(E)-ethyloxycarbonyloxycinnamoyl chloride in 15 ml of pyridine while stirring at 0° C. within 15 minutes. The reaction mixture was stirred at room temperature for a further 12 hours, then poured into water and extracted three times with 50 ml of ethyl acetate each time. The combined organic phases were dried over magnesium sulphate, filtered and subsequently concentrated. Chromatographic purification on silica gel with hexane/ethyl acetate (vol. 7:3) gave 3 g of 4-methacryloyloxybutyl (E)-3-(4-ethoxycarbonyloxyphenyl)acrylate, m.p. 54°-56° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. distillationSubsequently, excess thionyl chloride was distilled off
  3. addition3.3 g of 4-hydroxybutyl methacrylate were added dropwise to a solution of the resulting 4-(E)-ethyloxycarbonyloxycinnamoyl chloride in 15 ml of pyridine
  4. stirringThe reaction mixture was stirred at room temperature for a further 12 hours
  5. additionpoured into water
  6. extractionextracted three times with 50 ml of ethyl acetate each time
  7. dry with materialThe combined organic phases were dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationsubsequently concentrated
  10. customChromatographic purification on silica gel with hexane/ethyl acetate (vol. 7:3)

Sources & evidence

ORD record
ord-35df1e4e10354492bf662be6aad488f4
Source dataset
uspto-grants-2000_03
Patent number
USRE036625

Reaction notes

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