Hydrochloric Acid → 2-n-Butyl-3-methoxy-5,6-methylenedioxyindene

HRID 34708Notes

Reaction equation

HRID 34708 reaction equation
[CH2:1]([C:5](=[CH:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:16][O:17][C:11]=2[CH:10]=1)[CH:6]=[O:7])[CH2:2][CH2:3][CH3:4].Cl.[CH3:19]O>>[CH2:1]([C:5]1[CH2:8][C:9]2[C:14]([C:6]=1[O:7][CH3:19])=[CH:13][C:12]1[O:15][CH2:16][O:17][C:11]=1[CH:10]=2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 537308032-n-Butyl-3-(3,4-methylenedioxyphenyl)acrylaldehyde

Product 1

HCID 198442392-n-Butyl-3-methoxy-5,6-methylenedioxyindeneYield 90%

Procedure

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%).

Workup

  1. customUpon confirmation of full consumption of the raw material by thin-layer chromatography (eluent
  2. additiona 5:1 mixture of n-hexane and ether), the
  3. custombubbling of hydrogen chloride gas
  4. additionWater was added to the reaction mixture
  5. extractionfollowed by extraction of the resultant mixture with ether
  6. washAfter the resultant ether solution was washed with water
  7. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water successively, the ether solution was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (eluent
  10. additiona 10:1 mixture of n-hexane and ether)

Sources & evidence

ORD record
ord-18f014511b494430989f1ab0a6cae83a
Source dataset
uspto-grants-1988_08
Patent number
US04762927

Reaction notes

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