Sulfuric Acid → 4,5-(Dimethylmethylenedioxy)-3-(1-ethoxyethoxy)-6-heptenal

HRID 1741957Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[O:18][CH:15]([CH:16]=[CH2:17])[CH:4]([CH:5]([O:9][CH:10]([O:12][CH2:13][CH3:14])[CH3:11])[CH2:6][C:7]#N)[O:3]1.[H-].C([Al+]CC(C)C)C(C)C.S(=O)(=O)(O)[OH:31]>C1(C)C=CC=CC=1.CCOCC>[CH3:1][C:2]1([CH3:19])[O:18][CH:15]([CH:16]=[CH2:17])[CH:4]([CH:5]([O:9][CH:10]([O:12][CH2:13][CH3:14])[CH3:11])[CH2:6][CH:7]=[O:31])[O:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

4,5-(Dimethylmethylenedioxy)-3-(1-ethoxyethoxy)-6-heptenenitrile (1.40 g) was dissolved in 13 ml of dry toluene, and 2.0 ml of 2N diisobutyl aluminum hydride was added dropwise at -78° C. After stirring at -78° C. for 100 minutes, the temperature was then elevated to 0° C., and 10% dilute sulfuric acid was then gradually added. The reaction mixture was diluted with ether, and the organic layer was washed with a sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 2.61 g of 4,5-(dimethylmethylenedioxy)-3-(1-ethoxyethoxy)-6-heptenal.

Workup

customwas then elevated to 0° C.
washthe organic layer was washed with a sodium chloride aqueous solution
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-1c9818df3ef0427bac4c13de75620628
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334740

Reaction notes

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