Nitric Acid → Phthalaldehyde

Participants

Reaction Conditions

Reaction Steps

In a 1000-ml three-neck flask equipped with a thermometer, a reflux condenser and a stirrer were placed 13.3 g of o-xylylene glycol, 36.7 g of o-xylylene oxide, 85.1 g of 60% by weight nitric acid, 165.5 g of water, and 199.5 g of acetic acid. The mixture was raised in temperature to 70° C. on an oil bath and was stirred under these conditions for 1 hour. 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 84%. The obtained reaction mixture was extracted with two portions of toluene, the organic layer was distilled and thereby yielded phthalaldehyde in a yield of 67% on the basis of o-xylylene glycol. Gas chromatographic analysis revealed that phthalaldehyde had a purity of 98.8%. In addition, phthalide was formed in a yield of 11%.

Provenance & Evidence