Thionyl Chloride → HCID 19384698, compound

HRID 2399774Notes

Reaction equation

HRID 2399774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][C:6]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)([CH3:10])[C:7]([OH:9])=O.S(Cl)(Cl)=O>CCCCCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:18](=[CH:19][CH:20]=1)[C:7](=[O:9])[C:6]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)([CH3:10])[CH2:5]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19384700HCID 19384700, compound

Product 1

HCID 19384698HCID 19384698, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 2-(3-chlorobenzyl)-2-(4-chlorophenyl)propionic acid (10 g) which had been prepared in paragraph 2), and thionyl chloride (14 g) in hexane (100 ml) was heated under reflux for 5 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in carbon disulfide (100 ml), and the solution was cooled with ice, to which anhydrous aluminum chloride (4.2 g) was added in three portions at intervals of 15 minutes. After allowing the temperature to gradual increase to room temperature, the reaction mixture was diluted with dichloromethane (100 ml), poured into 20% hydrochloric acid and ice-water, followed by stirring for 2 hours. The organic layer was dried over anhydrous magnesium sulfate, and reduced under reduced pressure. The resulting residue was subjected to chromatography on silica gel to give 5-chloro-2-(4-chlorophenyl)-2-methyl-2,3-dihydro-1H-inden-1-one (yield, 7.2 g) as white crystals, m.p., 92.2° C,.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in carbon disulfide (100 ml)
  5. temperaturethe solution was cooled with ice, to which anhydrous aluminum chloride (4.2 g)
  6. additionwas added in three portions at intervals of 15 minutes
  7. temperatureto gradual increase to room temperature
  8. additionthe reaction mixture was diluted with dichloromethane (100 ml)
  9. additionpoured into 20% hydrochloric acid and ice-water
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-5d0efe87ceca4d33b0e180288fc472ec
Source dataset
uspto-grants-1995_09
Patent number
US05451607

Reaction notes

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