Hydrochloric Acid → HCID 2806137, compound

HRID 1579607Notes

Reaction equation

HRID 1579607 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])N.Cl.N([O-])=O.[Na+].[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]([CH3:22])=[O:21]>O.CC(C)=O>[CH3:22][C:20]([C:16]1[O:15][C:19]([C:4]2[CH:6]=[CH:7][C:8]([Cl:9])=[C:2]([Cl:1])[CH:3]=2)=[CH:18][CH:17]=1)=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 72573,4-DichloroanilineHCID 145052-AcetylfuranHCID 23668193Sodium Nitrite

Product 1

HCID 2806137HCID 2806137, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent3×

Procedure

A mixture of 81 g (0.50 mole) of 3,4-dichloroaniline, 100 ml of water and 75 ml of conc. HCl was heated on a steam bath to ca. 70°, and 150 ml of conc. HCl was added. White crystals separated and the mixture was cooled to 0°. A solution of 35 g (0.50 mole) of sodium nitrite in 150 ml of water was added at 0°-5° over 25 min and stirring was continued at 0°-5° for 1 hour. A solution of 55 g (0.50 mole) of methyl 2-furyl ketone in 50 ml of acetone was added quickly followed by the dropwise addition over 10 minutes at 4°-5° of a solution of 10 g (0.06 mole) of cupric chloride dihydrate in 20 ml of water. The cooling bath was removed, and the green solution was stirred overnight at ambient temperature. The solid which was deposited was collected by filtration and washed with water. Recrystallization from ca. 800 ml of MeOH gave 45 g (35%) of 5-(3,4-dichlorophenyl)-2-furyl methyl ketone A. Two additional recrystallizations from MeOH gave an analytical sample, m.p. 114°-117°.

Workup

  1. temperaturewas heated on a steam bath to ca. 70°
  2. customWhite crystals separated
  3. temperaturethe mixture was cooled to 0°
  4. customThe cooling bath was removed
  5. stirringthe green solution was stirred overnight at ambient temperature
  6. filtrationThe solid which was deposited was collected by filtration
  7. washwashed with water
  8. customRecrystallization from ca. 800 ml of MeOH

Sources & evidence

ORD record
ord-0efb01eb3ccf4edba65ba2f61f4fef51
Source dataset
uspto-grants-1976_01
Patent number
US03931247

Reaction notes

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