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

HRID 263614Notes

Reaction equation

HRID 263614 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-(ρ-methoxyphenyl)propionic acid (15 g.) is added to polyphosphoric acid (170 g.) at 50° C. and the mixture is heated at 83°-90° for two hours. 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 with 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 two hours
  2. extractionextracted with ether three times
  3. washThe ether solution is washed with water twice
  4. customwith 5% 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-9b0f8e4202e347eaae7a999e1675d815
Source dataset
uspto-grants-1997_07
Patent number
US05643959

Reaction notes

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