Methyl Acrylate → HCID 21079442, compound
Reaction equation
[CH3:1][CH:2]([CH3:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[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:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])([C:3](=[O:10])[CH:2]([CH3:1])[CH3:11])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
12.0 g (0.08 mol) of ethyl 4-methyl-3-oxo-pentanoate and 0.5 g (0.003 mol) of DBU were placed in a three necked round bottom flask, equipped-with dropping funnel and reflux condenser. At room temperature, 16.0 g (0.18 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 was neutral. The organic layer was dried over sodium sulfate, the solvent was removed, and the addition product was isolated by fractional distillation in a vacuum. 15.0 g (0.045 mol) of 4-(ethoxycarbonyl)-4-(2-methyl-1-oxopropyl)-heptanedioic acid 1,7-dimethyl ester was obtained (yield: 56%; boiling point: 145° C. at 0.02 mbar; colorless).
Workup
- temperaturereflux condenser
- customAt room temperature
- washwas washed with diluted hydrochloric acid
- washwas subsequently washed with distilled water until the aqueous layer
- dry with materialThe organic layer was dried over sodium sulfate
- customthe solvent was removed
- customthe addition product was isolated by fractional distillation in a vacuum
Sources & evidence
- ORD record
- ord-48f4518df1404a2dae24378b0559ee6a
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07166648B2
Reaction notes
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