3-(2-Chlorophenyl)propanoic acid → 4-chloro-2,3-dihydro-1H-inden-1-one

HRID 1645909Notes

Reaction equation

HRID 1645909 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=O>O>[Cl: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 956763-(2-Chlorophenyl)propanoic acid

Product 1

HCID 113326814-chloro-2,3-dihydro-1H-inden-1-oneYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 200 ml of polyphosphoric acid and 23.6 g (128 mmol) of 3-(2-chlorophenyl)-propanoic acid was heated on the steam bath for six hours. The mixture was allowed to cool, diluted with 500 ml of water, and the resulting solid collected. The solid was partitioned between ether and saturated sodium bicarbonate, the ether layer was separated, dried (MgSO4), and concentrated to a solid. The solid was crystallized from ether/hexane to give 7.8 g (37%) of 4-chloro-2,3-dihydro-1H-inden-1-one; mp 89°-92°.

Workup

  1. temperaturewas heated on the steam bath for six hours
  2. temperatureto cool
  3. customthe resulting solid collected
  4. customThe solid was partitioned between ether and saturated sodium bicarbonate
  5. customthe ether layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a solid
  8. customThe solid was crystallized from ether/hexane

Sources & evidence

ORD record
ord-25185ce94d624879a8f54d590a76c7b4
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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