Water → HCID 14204211, compound

HRID 231385Notes

Reaction equation

HRID 231385 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:12](=[O:14])[C:11]3[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=3[CH:9]=[CH:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 54519759HCID 54519759, compound

Product 1

HCID 14204211HCID 14204211, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 500 g (1.933 mol) of (E/Z)-2-[2-(3-chlorophenylethenyl]benzoic acid (in a ratio of about 23:77) in 500 ml of methylene chloride were added dropwise with stirring at the reflux temperature 241.6 g (2.031 mol) of thionyl chloride in the course of 1 hour and stirred in for 1 hour. Thereafter a suspension of 333 g (2.497 mol) of anhydrous aluminum chloride in 100 ml of methylene chloride was added at room temperature in the course of 45 min and stirred in at room temperature for 30 min, and the reaction mixture was then poured with stirring onto a mixture of 3 kg of ice and 1 l of water. The hydrolysis mixture was stirred for about 30 min. 1 l of petroleum ether (boiling range from 40° to 60° C.) was then added with stirring. The mixture was stirred for a further 30 min and then filtered with suction. The filter residue was washed first with 5 l of water and then with 1 l of petroleum ether (boiling range from 40° to 60° C.) and dried. 270 g were isolated of 2-chloro-5H-dibenzo-[a,d]cyclohepten-5-one in 58% yield; melting point 160°-161° C.

Workup

  1. additionwas added at room temperature in the course of 45 min
  2. stirringstirred in at room temperature for 30 min
  3. additionthe reaction mixture was then poured
  4. stirringThe hydrolysis mixture was stirred for about 30 min
  5. stirringwith stirring
  6. stirringThe mixture was stirred for a further 30 min
  7. filtrationfiltered with suction
  8. washThe filter residue was washed first with 5 l of water
  9. dry with materialwith 1 l of petroleum ether (boiling range from 40° to 60° C.) and dried

Sources & evidence

ORD record
ord-66aa4a1551674c30961126144bc08259
Source dataset
uspto-grants-1989_07
Patent number
US04845302

Reaction notes

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