Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dabco | HCID 9237 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Fluorooctanoic acid | HCID 14419501 | — |
| Reactant | Phenol, 4-(5-decyl-2-pyrimidinyl)- | HCID 135585902 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | HCID 14419502 | HCID 14419502 | 64% |
Reaction Steps
More specifically, 0.24 mg (1.5 mmol) of 2-fluorooctanoic acid was added to 2 ml of thionyl chloride and the mixture was refluxed at 90° C. for 2 hours. Then, the excess of thionyl chloride was distilled off, and a preliminarily prepared solution of 0.34 g (3.0 mmol) of triethylenediamine and 0.47 g (1.5 mmol) of 5-n-decyl-2-(p-hydroxyphenyl)pyrimidine in 5 ml of dry benzene was quickly added thereto, followed by 2 hours of stirring at 50° C. Thereafter, 0.06 g (1.5 mmol) of sodium hydride (60%) was added, and the mixture was further refluxed for 2 hours at 90° C. After the reaction, 2N-hydrochloric acid was added to the system, which was then subjected to extraction with benzene. The extract was dried, subjected to distillation of the solvent and purified by column chromatography with benzene to obtain 0.44 g (0.96 mmol) of 5-n-decyl-2-[4-(2-fluorooctanoyloxy)phenyl]pyrimidine. Yield: 64%
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04904410 |
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| Source dataset | uspto-grants-1990_02 |
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| ORD ID | ord-b6b8cd297f2e42569873dc4d4562d6b6 |
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| Source note | uspto-grants-1990_02 |
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