Hydrochloric Acid → 4-Acetyl-2'-nitrobiphenyl

HRID 436617

Reaction equation

HRID 436617 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:11])=[O:10].Cl>C(Cl)Cl>[C:5]([C:21]1[CH:20]=[CH:19][C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N+:9]([O-:11])=[O:10])=[CH:23][CH:22]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 68292-NitrobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 798054-Acetyl-2'-nitrobiphenyl

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 96.0 g. of aluminum chloride and 135 ml. of methylene chloride is stirred and treated with a mixture of 60 ml. of methylene chloride, 63 ml. of acetyl chloride, and 77.4 g. of 2-nitrobiphenyl. The mixture is heated at reflux for three hours and cautiously poured into 1200 g. of ice and 900 ml. of concentrated hydrochloric acid. The mixture is extracted with methylene chloride. The extract is washed with water and aqueous sodium bicarbonate, dried (Na2SO4), and the solvent removed to give a dark oil. This is stirred with 200 ml. of ether and the resulting solid recovered and washed with 1:1 ether:Skellysolve B; yield 53.50 g., m.p. 106°-109°. For analysis a sample is recrystallized from ether; m.p. 108°-111°.

Workup

  1. additionA suspension of 96.0 g
  2. additiontreated with a mixture of 60 ml
  3. temperatureThe mixture is heated
  4. temperatureat reflux for three hours
  5. additioncautiously poured into 1200 g
  6. extractionThe mixture is extracted with methylene chloride
  7. washThe extract is washed with water and aqueous sodium bicarbonate
  8. dry with materialdried (Na2SO4)
  9. customthe solvent removed
  10. customto give a dark oil
  11. customof ether and the resulting solid recovered
  12. washwashed with 1:1 ether
  13. customFor analysis a sample is recrystallized from ether

Sources & evidence

ORD record
ord-a4fc0df14eba48dc991f42ad3a2b1ac7
Source dataset
uspto-grants-1977_02
Patent number
US04009283

Linked notes

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