HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Aminophenol → 2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Aminophenol | HCID 5801 | — |
| Reactant | Propanoic acid, 2-bromo-2-methyl-, ethyl ester | HCID 11745 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Catalyst | Benzyl triethylammonium chloride | HCID 66133 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-one | HCID 10607395 | — |
Reaction Steps
3 g of 2-aminophenol is mixed in 23 ml of toluene with 1.8 g of sodium hydride with the addition of 50 mg of TEBA (triethylbenzylammonium chloride), and 4.4 ml of 2-bromo-2-methylpropionic acid ethyl ester is added drop by drop at ice bath temperature. After 2 hours at room temperature, it is poured onto ice water, extracted with ethyl acetate, washed with brine, the organic phase is dried with magnesium sulfate and concentrated by evaporation. After recrystallization from isopropyl ether, 278 mg of crystals results.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06191127B1 |
| Source dataset | uspto-grants-2001_02 |
| ORD ID | ord-b21f562c13d44f9aaf28a96bc0a9bde9 |
| Source note | uspto-grants-2001_02 |