Methyl Acrylate → HCID 58784961, compound

HRID 1375106Notes

Reaction equation

HRID 1375106 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14]>C1CCN2C(=NCCC2)CC1.C1CCCCC1>[CH3:17][O:16][C:12](=[O:15])[CH2:13][CH2:14][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])([C:2](=[O:1])[CH2:9][CH2:10][CH3:11])[CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 7294Methyl AcrylateHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 58784961HCID 58784961, compoundYield 115.4%

Reagents, catalysts & solvents 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 8078CyclohexaneSolvent

Conditions

Temperature
60 °C

Procedure

41.2 g (0.26 mol) of ethyl 3-oxo-hexanoate and 1.9 g (0.012 mol) of DBU were placed in a three necked round bottom flask, equipped with dropping funnel and reflux condenser. At room temperature, 56.3 g (0.65 mol) of methyl acrylate was slowly added drop by drop. After the exothermal behavior of the reaction leveled off, the reaction mixture was stirred at 60° C. for an additional two hours. The mixture was poured into cyclohexane and was washed with diluted hydrochloric acid and was subsequently washed with distilled water until the aqueous layer showed a neutral reaction. The organic layer was dried with sodium sulfate, the solvent was removed, and the residual addition product was isolated by fractional distillation in a vacuum. 50.0 g (0.15 mol) of 4-(ethoxycarbonyl)-4-(1-oxobutyl)-heptanedioic acid 1,7-dimethyl ester was obtained (yield: 58%; boiling point: 149° C. at 0.007 mbar; colorless).

Workup

  1. customequipped
  2. temperaturereflux condenser
  3. customAt room temperature
  4. washwas washed with diluted hydrochloric acid
  5. washwas subsequently washed with distilled water until the aqueous layer
  6. customa neutral reaction
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. customthe solvent was removed
  9. customthe residual addition product was isolated by fractional distillation in a vacuum

Sources & evidence

ORD record
ord-c7f62af7603b4d89a2def6109e7802d5
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

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