Reaktion #62986

Reaktionsgleichung

2-n-butyl-3-(3,4-methylenedioxyphenyl)acrylaldehyde

hydrogen chloride

methanol

→

2-n-butyl-3-methoxy-5,6-methylenedioxyindene

Ausbeute 90.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeUpon confirmation of full consumption of the raw material by thin-layer chromatography (eluent
2. 2
   workup.ADDITIONa 5:1 mixture of n-hexane and ether), the
3. 3
   Sonstigebubbling of hydrogen chloride gas
4. 4
   workup.ADDITIONWater was added to the reaction mixture
5. 5
   Extraktionfollowed by extraction of the resultant mixture with ether
6. 6
   WaschenAfter the resultant ether solution was washed with water
7. 7
   Trocknena saturated aqueous solution of sodium hydrogencarbonate and water successively, the ether solution was dried over anhydrous magnesium sulfate
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThe residue was purified by column chromatography on silica gel (eluent
10. 10
    workup.ADDITIONa 10:1 mixture of n-hexane and ether)

Vorschrift

Dissolved in 80 ml of methanol was 12 g of 2-n-butyl-3-(3,4-methylenedioxyphenyl)acrylaldehyde, into which hydrogen chloride qas was blown under ice-salt cooling. Upon confirmation of full consumption of the raw material by thin-layer chromatography (eluent: a 5:1 mixture of n-hexane and ether), the bubbling of hydrogen chloride gas was stopped. Water was added to the reaction mixture, followed by extraction of the resultant mixture with ether. After the resultant ether solution was washed with water, a saturated aqueous solution of sodium hydrogencarbonate and water successively, the ether solution was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: a 10:1 mixture of n-hexane and ether) to give 11.4 g of 2-n-butyl-3-methoxy-5,6-methylenedioxyindene as an oily substance (yield: 90%).

Quelle