Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Crotonic Acid | HCID 637090 | — |
| Reactant | HCID 53749111 | HCID 53749111 | — |
| Catalyst | p-Toluenesulfonic acid | HCID 6101 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86762527 | HCID 86762527 | 53.5% |
Reaction Steps
The obtained 4,5-dimethyl-hexan-2-ol (296 g), crotonic acid (391 g,), PTSA (3 g), and toluene (300 mL) were charged into a 2-L reaction flask fitted with a mechanical stirrer, a thermocouple, a Dean-Stark trap, and a condenser. The reaction mixture was heated to reflux at about 120-130° C. Water was removed azeotropically. The reaction was aged at reflux for about 4-5 hours until no more water evolved. The reaction was cooled to room temperature and quenched with water (400 mL). The organic layer was separated and subsequently washed with sodium carbonate (5%, 300 mL), and further fractional distilled to provide but-2-enoic acid 1,3,4-trimethyl-pentyl ester (241 g) with a boiling point of 108° C. at 13 mmHg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08772533B1 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-b5ac33b4372647b39f0f7de5138bac1a |
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| Source note | uspto-grants-2014_07 |
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