Hydrochloric Acid → Benzophenone

HRID 529861Notes

Reaction equation

HRID 529861 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+]([O-])=O)=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClCCl>[C:4]([C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]=1)(=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 3102Benzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[13C6]-Benzene (0.6 g, 7.1 mmol) was added to a solution of 2-chloro-5-nitrobenzoic acid chloride (3.13 g, 14.3 mmol) in 50 mL of dichloromethane. The mixture was cooled to 0-5° C. before AlCl3 (2.29 g, 17.2 mmol) was added in slowly. Upon completion of the addition, the mixture was allowed to reach room temperature, and stirring was continued for 24 h. The deep-red solution was treated with HCl and ice, and the resulting aqueous phase was extracted with ether. The combined organic extracts were washed with 2% aqueous NaOH and then water and dried over sodium sulphate. The solvent was removed in vacuo to give crude benzophenone, which was recrystallized from toluene/isopropyl ether to yield 1.52 g (80%) of pure [13C6]-2-chloro-5-nitrobenzophenone.

Workup

  1. additionwas added in slowly
  2. additionUpon completion of the addition
  3. customto reach room temperature
  4. extractionthe resulting aqueous phase was extracted with ether
  5. washThe combined organic extracts were washed with 2% aqueous NaOH
  6. dry with materialwater and dried over sodium sulphate
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-72a73921d4d24d7cb8ceb111a53ab150
Source dataset
uspto-grants-2016_05
Patent number
US09347961B2

Reaction notes

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