Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl Acrylate | HCID 7294 | — |
| Reactant | Ethyl 3-oxohexanoate | HCID 238498 | — |
| Catalyst | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Product | HCID 58784961 | HCID 58784961 | 115.4% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07166648B2 |
|---|
| Source dataset | uspto-grants-2007_01 |
|---|
| ORD ID | ord-c7f62af7603b4d89a2def6109e7802d5 |
|---|
| Source note | uspto-grants-2007_01 |
|---|