Nitric Acid → Phthalaldehyde
Reaction equation
[C:1]12[CH2:9][O:8][CH2:7][C:2]1=[CH:3][CH:4]=[CH:5][CH:6]=2.[N+]([O-])(O)=[O:11].O>C(O)(=O)C>[CH:7](=[O:11])[C:2]1[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:9]=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
In a 1000-ml three-neck flask equipped with a thermometer, a reflux condenser and a stirrer were placed 50 g of o-xylylene oxide, 43.8 g of 60% by weight nitric acid, 203.1 g of water, and 220.6 g of acetic acid. The mixture was raised in temperature to 70° C. on an oil bath and was stirred under these conditions for 4 hours. After cooling, the reaction mixture was analyzed by gas chromatography to find that the raw material o-xylylene oxide was completely absent and that phthalaldehyde was formed in a yield of 50%. The obtained reaction mixture was extracted with two portions of toluene, the organic layer was distilled and thereby yielded phthalaldehyde in a yield of 35% on the basis of o-xylylene oxide. Gas chromatographic analysis revealed that phthalaldehyde had a purity of 93.0%. In addition, phthalide was formed in a yield of 9%.
Workup
- customIn a 1000-ml three-neck flask equipped with a thermometer, a reflux condenser and a stirrer
- temperatureAfter cooling
Sources & evidence
- ORD record
- ord-205a502bcc9d4d418bedd87172219bef
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797844B2
Reaction notes
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