2,6-Dichlorobenzaldehyde → 4-Methoxy-2-(2', 6'-Dichlorophenyl)indan-1,3-dione

HRID 1076125Notes

Reaction equation

HRID 1076125 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[CH3:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][O:16][C:17]2=[O:18].C[O-].[Na+]>C(OCC)(=O)C.CO>[CH3:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15](=[O:16])[CH:4]([C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10])[C:17]2=[O:18]

Participants

6

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 10942334Sodium MethoxideHCID 111163794-METHOXYISOBENZOFURAN-1(3H)-ONE

Product 1

HCID 537867074-Methoxy-2-(2', 6'-Dichlorophenyl)indan-1,3-dioneYield 82.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,6-dichlorobenzaldehyde (5.98 grams, 0.034 mole) and 4-methoxyphthalide (5.6 grams, 0.34 mole) in 20.5 milliliters of ethyl acetate was added to a solution of sodium methoxide in methanol (prepared from 2.36 grams of sodium metal and 34 milliliters of methanol). The mixture was then heated under reflux for 1 hour. The bulk of the ethyl acetate and methanol was removed under reduced pressure. The residue was dissolved in water and the solution filtered from insoluble material. Acidification of the filtered alkaline solution afforded 9.0 grams of a yellow solid which was recrystallized from ethanol to give 6.5 grams (59.3%) of the title compound, melting point 163°-165°C. Calc'd: C, 59.83, H, 3.14; Found: C, 59.55, H, 3.19.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 1 hour
  3. customThe bulk of the ethyl acetate and methanol was removed under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. filtrationthe solution filtered from insoluble material

Sources & evidence

ORD record
ord-e8ad99ef34d748a8a849ec2d7f01031e
Source dataset
uspto-grants-1976_05
Patent number
US03954998

Reaction notes

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