Hydrochloric Acid → HCID 12585191, compound

HRID 2285612Notes

Reaction equation

HRID 2285612 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:9]([C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1)([O-:11])=[O:10].[Cl-:21].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([C:4]2[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[C:2]([Cl:21])[CH:3]=2)=[O:17])=[CH:19][CH:20]=1)([O-:11])=[O:10].[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([C:4]2[CH:5]=[CH:6][C:1]([O:7][CH3:8])=[CH:2][C:3]=2[Cl:21])=[O:17])=[CH:19][CH:20]=1)([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 2

HCID 12585191HCID 12585191, compoundHCID 12585195HCID 12585195, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of anisole (8.67 g., 0.08 mole), 4-nitrobenzoyl chloride (16.4 g., 0.088 mole) and methylene chloride (80 ml). at 5° was stirred vigorously and treated with finely powdered aluminum chloride (11.2 g., 0.084 mole). The reaction mixture was stirred at room temperature for 20 hrs. and then decomposed with ice and hydrochloric acid (15 ml.). The aqueous solution was extracted twice with methylene chloride. The combined methylene chloride solution was washed with aqueous sodium bicarbonate solution and finally with water. The organic layer was dried (MgSO4) and filtered. The solvent was removed in vacuo, and the residue on triturating with methanol gave the product, m.p. 121°-122°. This product was used in the next step without purification. 4-(4-nitrobenzoyl)-2-chloroanisole and 4-(4-nitrobenzoyl)-3-chloroanisole were prepared by the same procedure.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 20 hrs
  2. extractionThe aqueous solution was extracted twice with methylene chloride
  3. washThe combined methylene chloride solution was washed with aqueous sodium bicarbonate solution and finally with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe residue on triturating with methanol
  8. customgave the product, m.p. 121°-122°
  9. customThis product was used in the next step without purification

Sources & evidence

ORD record
ord-0d704e06f7894b6eb377c0ede604b5aa
Source dataset
uspto-grants-1982_04
Patent number
US04323691

Reaction notes

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