Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methacryloyl chloride | HCID 13528 | — |
| Reactant | N-(3-hydroxypropyl)acetamide | HCID 2781177 | — |
| Catalyst | 2,6-Di-tert-butyl-4-methylphenol | HCID 31404 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 15055173 | HCID 15055173 | 53.4% |
Reaction Steps
184.0 g (1.76 mol) of methacryloyl chloride were added dropwise in the course of 2 hours to an initial mixture, cooled to -72° C., consisting of 206.2 g (1.76 mol) of N-(3-hydroxypropyl)-acetamide, 750 ml of methylene chloride, 228 g (2.25 mol) of triethylamine and 250 mg of 2,6-di-tert.butyl-4-methylphenol. The mixture was stirred for a further 2 hours at -52° C. and the precipitated pale precipitate was then filtered off with suction at 0° C. The filtrate was subjected to aqueous work-up and the product was dried and, after concentrating on a rotary evaporator, distilled first at 100° C., and then the residue at 130° C. (in each case 0.1 mm Hg). 174.1 g (53% of theory) of 3- acetamidopropyl methacrylate were obtained in the form of a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05300537 |
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| Source dataset | uspto-grants-1994_04 |
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| ORD ID | ord-dbee653892a94d3981ad2cabc6b45da6 |
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| Source note | uspto-grants-1994_04 |
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