3-(2-Methylphenyl)propionic acid → 4-Methyl-1-indanone

HRID 1645905Notes

Reaction equation

HRID 1645905 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH2:9][C:10]2=[O:12]

Participants

3

Reactant 1

HCID 309383-(2-Methylphenyl)propionic acid

Product 1

HCID 44184314-Methyl-1-indanoneYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 12.0 g (73.2 mmol) of 2-methylbenzenepropanoic acid in 125 ml of methylene chloride was added portion-wise to 500 g of polyphosphoric acid. The mixture was heated for six hours on the steam bath and the resulting orange solution was diluted with 1.5 l of ice. The solid was collected, washed with water, and air dried to give 7.2 g crude material. Recrystallization from ethanol/water gave 5.8 g of the desired product; mp 94°-97°. Extraction of the original diluted reaction mixture with methylene chloride gave an additional lot. Total recovery was 7.7 g (72%).

Workup

  1. temperatureThe mixture was heated for six hours on the steam bath
  2. customThe solid was collected
  3. washwashed with water, and air
  4. customdried
  5. customto give 7.2 g crude material
  6. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-bff92f0b60da466b9358fd8ef8186b4d
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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