Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl Acrylate | HCID 7294 | — |
| Reactant | Methyl 3-oxovalerate | HCID 121699 | — |
| Catalyst | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Product | HCID 58784963 | HCID 58784963 | 129% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07166648B2 |
|---|
| Source dataset | uspto-grants-2007_01 |
|---|
| ORD ID | ord-a83af03af1b049ae8a861c7950089092 |
|---|
| Source note | uspto-grants-2007_01 |
|---|