3-(2,4-Dichlorophenyl)propanoic acid → 4,6-Dichloro-1-indanone

HRID 430070Notes

Reaction equation

HRID 430070 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([OH:13])=O>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]2[C:3]=1[CH2:9][CH2:10][C:11]2=[O:13]

Participants

3

Reactant 1

HCID 27409153-(2,4-Dichlorophenyl)propanoic acid

Product 1

HCID 122065184,6-Dichloro-1-indanoneYield 4.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(2,4-dichlorophenyl)propanoic acid (0.44 g, 2 mmol) in polyphosphoric acid (7 g) was heated to 100° C. under argon. After 90 min the mixture was cooled and treated with water (20 ml) and extracted with hexane (40 ml). The hexane layer was dried (MgSO4), and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 0-30% dichloromethane in hexane to give the title product as a yellow solid, (0.018 g, 4.5%), δH (CDCl3) 2.8 (2H, m), 3.1 (2H, m), 7.6 (1H, d), 7.65 (1H, d).

Workup

  1. temperatureAfter 90 min the mixture was cooled
  2. extractionextracted with hexane (40 ml)
  3. dry with materialThe hexane layer was dried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel eluting with 0-30% dichloromethane in hexane

Sources & evidence

ORD record
ord-bdaed1af101f4a3fb37531108d241fdc
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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