HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetyl chloride → 2-Methyl-benzooxazole-4-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | Ethyl 2-amino-3-hydroxybenzoate | HCID 14167647 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-Methyl-benzooxazole-4-carboxylic acid ethyl ester | HCID 59316840 | — |
Reaction Steps
A mixture of 2-amino-3-hydroxy-benzoic acid ethyl ester (5.52 mmol; J. Reisch, G. M. K. B. Gunaherath Monatshefte für Chemie, 1988, 119, 1169-1178), acetyl chloride (6.07 mmol), NEt3 (6.07 mmo) and pyridinium p-toluenesulfonate (1.47 mmol) in xylene (60 mL) is heated at reflux for 16 h, cooled to rt, diluted with EtOAc and washed with water. The organic layer is dried over MgSO4 and concentrated in vacuo to give a crude product which is purified by flash chromatography (gradient: heptane to heptane/EtOAc 6/4). LC-MS: tR=0.81 min; [M+H]+=206.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08236801B2 |
| Source dataset | uspto-grants-2012_08 |
| ORD ID | ord-9c140c3a7bd94a99b0ac4d9bdce1a0ac |
| Source note | uspto-grants-2012_08 |