Nitric Acid → Phthalaldehyde
Reaction equation
[C:1]1([CH2:9][OH:10])[C:2]([CH2:7][OH:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[N+]([O-])(O)=O.O>C(O)(=O)C>[CH:9](=[O:10])[C:1]1[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:7]=[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 glycol, 39.2 g of 60% by weight nitric acid, 197.6 g of water, and 213.2 g of acetic acid. The mixture was raised in temperature to 70° C. on an oil bath and was stirred under these conditions for 2 hours. After cooling, the reaction mixture was analyzed by gas chromatography to find that the raw material o-xylylene glycol was completely absent and that phthalaldehyde was formed in a yield of 60%. In addition, phthalide (yield: 6%) and an ester of the raw material were formed as by-products. The obtained reaction mixture was extracted with two portions of toluene, the organic layer was distilled and thereby yielded phthalaldehyde in a yield of 45% on the basis of o-xylylene glycol. Gas chromatographic analysis revealed that phthalaldehyde had a purity of 95.0%. In addition, phthalide was formed in a yield of 10%.
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-29a0f964ba3e4bc39573c09f5ccace18
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797844B2
Reaction notes
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