Sulfuric Acid → 3,7-Dimethylocta-2,6-Dienal

Temperature

50 °C

346 mg (2 mmols) of geranyl chloride and 787 mg (6 mmols) of N-ethylmorpholine N-oxide were placed in a flask, to which was further added 3 ml of N,N-dimethylformamide. The mixture was agitated at room temperature for 1 hour and at 50° C. for 4 hours. To the reaction mixture was added 10 ml of 2.5% sulfuric acid and 10 ml of ethyl acetate for phase separation. The resultant organic phase was washed with 5 ml of 2.5% sulfuric acid, 5 ml of a saturated sodium hydrogen carbonate aqueous solution and 5 ml of a 10% sodium sulfate aqueous solution successively, after which it was dried with magnesium sulfate. After the drying, the solvent was distilled off from the solution and the residue was subjected to distillation by the use of Kugel-rohr distillation apparatus (bath temperature 93° C./3 Torr.) to obtain 268 mg (1.76 mmols) of citral. The yield was 88%.

1. customfor phase separation
2. washThe resultant organic phase was washed with 5 ml of 2.5% sulfuric acid, 5 ml of a saturated sodium hydrogen carbonate aqueous solution and 5 ml of a 10% sodium sulfate aqueous solution successively
3. dry with materialafter which it was dried with magnesium sulfate
4. distillationAfter the drying, the solvent was distilled off from the solution
5. distillationthe residue was subjected to distillation by the use of Kugel-rohr distillation apparatus (bath temperature 93° C./3 Torr.)

ORD record

ord-737cf806fb344cfc962b805f11395ba3

Source dataset

uspto-grants-1988_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04745229