Hydrochloric Acid → HCID 13911211, compound

HRID 652335Notes

Reaction equation

HRID 652335 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[OH:25].Cl>[N+](C1C=CC=CC=1)([O-])=O>[CH3:17][C:18]1[CH:23]=[C:22]([CH:21]=[C:20]([CH3:24])[C:19]=1[OH:25])[C:8]([C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 113352,6-DimethylphenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13911211HCID 13911211, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

To a stirring solution of p-nitrobenzoyl chloride (76.1 g, 0.410 mol) in 250 mL nitrobenzene were added 82 g of AlCl3 (0.62 mol). To this mixture a solution of 50 grams of 2,6-dimethylphenol (0.41 mole) in 250 mL nitrobenzene was added dropwise over a period of 45 minutes, and the resulting mixture was stirred 16 hours at room temperature. The reaction was poured into 2 L of 3% HCl and ice and extracted 3×1 L with Et2O (i.e. times with 1 L each time f diethyl ether). The combined ethereal layers were washed with 1 L of saturated NaHCO3, then extracted 2×1 L with 10% NaOH. The combined basic extracts were acidified with concentrated HCl to give a white precipitate; filtration followed by recrystallization from CH3OH/H2O gave 37 g (33%) of white powder consistent with the desired product by TLC, IR, mass spectroscopy, NMR and elemental analysis, m.p. 182.5-184.5.

Workup

  1. extractionextracted 3×1 L with Et2O (i.e. times with 1 L each time f diethyl ether)
  2. washThe combined ethereal layers were washed with 1 L of saturated NaHCO3
  3. extractionextracted 2×1 L with 10% NaOH
  4. customto give a white precipitate
  5. filtrationfiltration
  6. customfollowed by recrystallization from CH3OH/H2O

Sources & evidence

ORD record
ord-7e5424b59851459fa45185333648e0e4
Source dataset
uspto-grants-1987_06
Patent number
US04670572

Reaction notes

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