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

HRID 1609624Notes

Reaction equation

HRID 1609624 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-827e1fdbf2eb449ab908f20f257d1078
Source dataset
uspto-grants-1995_03
Patent number
US05401774

Reaction notes

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