HCID 11160380, compound → 6-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

HRID 461097

Reaction equation

HRID 461097 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([CH3:16])[C:11]([O:13]CC)=O)=[CH:5][CH:4]=1>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([CH2:9][CH:10]([CH3:16])[C:11]2=[O:13])=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 11160380HCID 11160380, compound

Product 1

HCID 2311786-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl β-(p-methoxyphenyl)-α-methylpropionate is added to 56 g of polyphosphoric acid with stirring at 50° C. The mixture is then heated to 83°-90° C for two hours. The cooled reaction mixture is poured slowly into a mixture of water and crushed ice with stirring and extracted with 3 × 300 ml of ether. The etheral solution is washed with 10% sodium bicarbonate solution followed by cold water to neutral, then with saturated sodium chloride solution and dried over magnesium sulfate for 1.5 hours and filtered. The solvent is removed on an evaporator and the residue distilled to obtain 6-methoxy-2-methylindanone.

Workup

  1. temperatureThe mixture is then heated to 83°-90° C for two hours
  2. customThe cooled reaction mixture
  3. customcrushed ice
  4. stirringwith stirring
  5. extractionextracted with 3 × 300 ml of ether
  6. washThe etheral solution is washed with 10% sodium bicarbonate solution
  7. dry with materialdried over magnesium sulfate for 1.5 hours
  8. filtrationfiltered
  9. customThe solvent is removed on an evaporator
  10. distillationthe residue distilled

Sources & evidence

ORD record
ord-4dfc247c4f014ead8560c679c455836a
Source dataset
uspto-grants-1977_12
Patent number
US04061771

Linked notes

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