Hydrochloric Acid → 4,5,6-Trimethoxy-2,3-dihydro-1H-inden-1-one

HRID 473065Notes

Reaction equation

HRID 473065 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[C:8]2[C:4]=1[CH:5](C1C=C(OC)C(OC)=C(OC)C=1)[CH2:6][C:7]2=[O:16].C1OC2C=CC(C=O)=CC=2O1.Cl>[OH-].[K+].O>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8438PiperonalHCID 24894048HCID 24894048, compound2×

Product 1

HCID 190217004,5,6-Trimethoxy-2,3-dihydro-1H-inden-1-oneYield 180.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
30 °C

Procedure

4,5,6-trimethoxy-3-(3,4,5-trimethoxyphenyl)-indan-1-one (formula 7, 250 mg) was taken in 2.5% methanolic potassium hydroxide (10 mL). To this stirred solution 3,4-methylenedioxybenzaldehyde (100 mg) was added and further stirred at room temperature at 30° C. for 1 hour. On completion, the reaction mixture was diluted with water, acidified with dil. HCl and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulphate and evaporated to get a residue. The residue was purified through silica gel column to get 2-benzo[1,3]dioxo-5-ylmethylene-4,5,6-trimethoxy-3-(3,4,5-trimethoxyphenyl)-indan-1-one (formula 8, 258 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated
  5. customto get a residue
  6. customThe residue was purified through silica gel column

Sources & evidence

ORD record
ord-95c12d6fd3f3431d83165fcd0441dcdf
Source dataset
uspto-grants-2014_01
Patent number
US08633242B2

Reaction notes

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