Hydrochloric Acid → 1H-Indene-1,3(2H)-dione, 2-(3-methoxyphenyl)-

HRID 527171

Reaction equation

HRID 527171 reaction equation
[Na].[C:2]1([C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][O:4]1)=[O:3].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O.Cl>C(O)C>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:17]2[C:2](=[O:3])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]2=[O:4])[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6885PhthalideHCID 115693-MethoxybenzaldehydeHCID 5360545Sodium

Product 1

HCID 28178101H-Indene-1,3(2H)-dione, 2-(3-methoxyphenyl)-Yield 44.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (1.1 g) was dissolved in anhydrous Ethanol (90 ml). This solution was added with Phthalide (4.43 g, 33.04 mmol) and m-Methoxy benzaldehyde (3.00 g, 22.03 mmol). The reaction mixture was heated for 3 hrs under reflux. The reaction mixture was concentrated in a vacuum. White solid was obtained by adding conc.HCl. And then the white solid was recrystalized in ethylacetate:hexane (=1:2) to afford the title compound (2.45 g, 44%).

Workup

  1. temperatureThe reaction mixture was heated for 3 hrs
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated in a vacuum
  4. customWhite solid was obtained
  5. additionby adding conc
  6. customAnd then the white solid was recrystalized in ethylacetate

Sources & evidence

ORD record
ord-a2cbd0cde9bf4e638eae4508bc2d74a6
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Linked notes

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