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

HRID 1954320Notes

Reaction equation

HRID 1954320 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

Conditions

Temperature
86.5 °C

Procedure

α-Methyl-β-(p-methoxyphenyl)propionic acid (15 g) is added to polyphosphoric acid (170 g) at 50° C. and the mixture is heated at 83-90° C. 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. extractionextracted with ether three times
  2. washThe ether solution is washed with water twice
  3. customwith 5% NaHCO3 five times until all the acidic material has been removed
  4. washThe remaining neutral solution is washed with water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solution

Sources & evidence

ORD record
ord-fff46b8d2d8042ec91a67f148ad066ad
Source dataset
uspto-grants-2000_09
Patent number
US06121321

Reaction notes

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