Methyl Acrylate → HCID 58784963, compound

HRID 1375104Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

39.9 g (0.31 mol) of methyl 3-oxo-pentanoate and 1.9 g (0.012 mol) of DBU were mixed at room temperature in a three necked round bottom flask, equipped with a dropping funnel and a reflux condenser. 66.4 g (0.77 mol) of methyl acrylate was slowly added drop by drop. After the exothermal behavior has leveled off, the reaction mixture was stirred at 60° C. for an additional two hours. Cyclohexane was added and the mixture 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 over sodium sulfate, the solvent was removed, and the addition product was isolated by fractional distillation in a vacuum. 21.4 g (0.20 mol) of 4-(methoxycarbonyl)-4-(1-oxopropyl)-heptanedioic acid 1,7-dimethyl ester was obtained (yield: 64%; boiling temperature: 130° C. at 0.02 mbar; colorless).

Workup

customequipped with a dropping funnel and a reflux condenser
washthe mixture was washed with diluted hydrochloric acid
washwas subsequently washed with distilled water until the aqueous layer
customa neutral reaction
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-a83af03af1b049ae8a861c7950089092
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166648B2

Reaction notes

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