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In a 5 L flask equipped with mechanical stirrer and reflux condenser were placed 100.0 g (0.657 mol) of 3.4-dimethoxytoluene, 2.64 L of cyclohexane (0.25 M), and 104.5 g (0.986 mol) of anhydrous sodium carbonate. The apparatus was flushed with argon. The mixture was stirred and heated to reflux while continuing to sweep argon gently over the solution. A mixture of 197.28 g of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH, 0.69 mol, 1.05 eq.) and 4.08 g 2,2'-azobis- 2,4-dimethylpentanenitrile (VAZO-52, 0.016 mol, 0.025 eq.) were gradually added through a funnel to the solution over a period of 120 minutes. After addition of the mixture was complete, the reaction mixture was allowed to stir for another thirty minutes at reflux. The solution was allowed to cool to room temperature and the solids was removed by vacuum filtration. The receiver flask contained 122.0 g of sodium carbonate monohydrate. The cyclohexane was removed in vacuo. To the residue was added 600 mL of water and 600 mL of tetrahydrofuran. The solution was mechanically stirred and heated to reflux for two hours. After cooling, the tetrahydrofuran was removed in vacuo. The aqueous solution was extracted three times with 200 mL of methyl tert-butyl ether. The organic extract was dried with anhydrous magnesium sulfate. After removing the magnesium sulfate by vacuum filtration through a fritted funnel, the methyl tert-butyl ether was removed in vacuo to provide 120.6 g of crude veratraldehyde (0.725 mol, 110.4% yield) that was shown to be 74.9% pure by GC and 77.4% pure by HPLC. The product was purified by bulb-to-bulb distillation to provide 72.2 g of veratraldehyde (0.434 mol, 66.1% yield, 94.1% pure by GC, 97.2% pure by HPLC). The distilled material was dissolved in 1.5 volumes (108 mL) of toluene and 1.5 volumes of cyclohexane and allowed to sit overnight in a freezer. The crystals were collected the following morning by vacuum filtration. The filter cake was washed liberally with cyclohexane. After drying in vacuo, 53.7 g (0.323 mol, 49.2% yield, 100.0% pure by HPLC, 99.2% pure by GC) of white crystalline veratraldehyde was collected.

1. customIn a 5 L flask equipped with mechanical stirrer
2. temperaturereflux condenser
3. customThe apparatus was flushed with argon
4. temperatureheated
5. temperatureto reflux
6. additionAfter addition of the mixture
7. stirringto stir for another thirty minutes
8. temperatureat reflux
9. customthe solids was removed by vacuum filtration
10. customThe cyclohexane was removed in vacuo
11. additionTo the residue was added 600 mL of water and 600 mL of tetrahydrofuran
12. stirringThe solution was mechanically stirred
13. temperatureheated
14. temperatureto reflux for two hours
15. temperatureAfter cooling
16. customthe tetrahydrofuran was removed in vacuo
17. extractionThe aqueous solution was extracted three times with 200 mL of methyl tert-butyl ether
18. extractionThe organic extract
19. dry with materialwas dried with anhydrous magnesium sulfate
20. customAfter removing the magnesium sulfate
21. filtrationby vacuum filtration through a fritted funnel
22. customthe methyl tert-butyl ether was removed in vacuo