3-(4-Methoxyphenyl)-2-methylpropanoic acid → 6-Methoxy-2-methyl-2,3-dihydro-1H-inden-1-one

HRID 1955711Notes

Reaction equation

HRID 1955711 reaction equation
[CH3:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[C:3]([OH:5])=O>O>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7]([CH2:6][CH:2]([CH3:1])[C:3]2=[O:5])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 105358043-(4-Methoxyphenyl)-2-methylpropanoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

α-Methyl-β-(p-methoxyphenyl)propionic acid (15 g) is added to 170 g of polyphosphoric acid at 50° and the mixture is heated at 83°-90° for 2 h. The syrup is poured into iced water, stirred for one-half hour and then extracted with ether three times. The ether solution is washed with water twice and 5% NaHCO3 five times until all the acidic material has been removed. The remaining neutral solution is washed with water and dried over sodium sulfate. Evaporation of the solution gives the indanone as a pale yellow oil.

Workup

  1. temperaturethe mixture is heated at 83°-90° for 2 h
  2. extractionextracted with ether three times
  3. washThe ether solution is washed with water twice
  4. custom5% NaHCO3 five times until all the acidic material has been removed
  5. washThe remaining neutral solution is washed with water
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solution

Sources & evidence

ORD record
ord-f7adac3230224419a634e1e5bf8d7195
Source dataset
uspto-grants-1998_07
Patent number
US05776962

Reaction notes

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