(4-Chlorophenyl)acetic acid → Ethanone, 2-(4-chlorophenyl)-1-phenyl-

HRID 436382Notes

Reaction equation

HRID 436382 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9](=[O:11])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 15880(4-Chlorophenyl)acetic acidHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 95829Ethanone, 2-(4-chlorophenyl)-1-phenyl-Yield 142.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A benzene solution containing 51.2 g 4-chlorophenylacetic acid and 39.3 g thionyl chloride is refluxed for 6 hours and the solvent removed. The crude reaction product is added dropwise to a slurry of 40 g aluminum chloride in 200 ml benzene maintaining the temperature below 50° C. After addition the reaction is refluxed for 1.5 hours. After cooling, the mixture is poured into ice and the resulting white solid is separated yielding 61.3 g of crude product. The product is taken up in methylene chloride and washed with 5% sodium hydroxide solution followed by water, dried over sodium sulfate and stripped yielding 49.3 g (71%) of >95% pure 4'-chlorodeoxybenzoin. 15 g of 4-chlorodeoxybenzoin is dissolved in 105 ml pyridine. An aqueous solution containing 15 g potassium permanganate is added and the reaction stirred for 6 hours at room temperature using dry ice to buffer the pH near 7. The mixture is extracted with methylene chloride, the extract washed with water, dried over Na2SO4 and stripped. The residue is recrystallized from ethanol yielding 6.1 g of white plate-like crystals which is identified as starting material. Concentration of the mother liquor yields 4 g of 4-chlorobenzil.

Workup

  1. temperatureis refluxed for 6 hours
  2. customthe solvent removed
  3. customThe crude reaction product
  4. additionAfter addition the reaction
  5. temperatureis refluxed for 1.5 hours
  6. temperatureAfter cooling
  7. additionthe mixture is poured into ice
  8. customthe resulting white solid is separated
  9. customyielding 61.3 g of crude product
  10. washwashed with 5% sodium hydroxide solution
  11. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-b51ce1ad36624850985a193b27954a53
Source dataset
uspto-grants-1977_02
Patent number
US04009022

Reaction notes

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