Hydrochloric Acid → HCID 18704048, compound

HRID 264590Notes

Reaction equation

HRID 264590 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:13][C:14]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:15]=1[C:16](Cl)=[O:17].Cl>O>[Cl:13][C:14]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:15]=1[C:16]([C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7809P-XyleneHCID 179452,5-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18704048HCID 18704048, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To p-xylene (120 ml, 0.98 mol) was added aluminum chloride (32 g, 0.24 mol) at room temperature. To this mixture 2,5-dichlorobenzoyl chloride (30 g, 0.14 mol) was added slowly. The reaction was exothermic and hydrogen chloride evolved from the reddish solution. After the addition, the mixture was stirred for 10 min and then hydrolysed by slow addition of water. The aqueous layer was extracted with ether. The organic layer was combined with ethereal extract and washed with water, saturated sodium bicarbonate, brine, respectively, and then dried with magnesium sulfate. After the removal of solvent, the residue was recrystallized from methanol twice and then from hexane to give 36.8 g (92%) crystals (mp 58°-61° C.).

Workup

  1. additionAfter the addition
  2. extractionThe aqueous layer was extracted with ether
  3. extractionwith ethereal extract
  4. washwashed with water, saturated sodium bicarbonate, brine
  5. dry with materialrespectively, and then dried with magnesium sulfate
  6. customAfter the removal of solvent
  7. customthe residue was recrystallized from methanol twice

Sources & evidence

ORD record
ord-031d3469d00f44d58d8923712be49edd
Source dataset
uspto-grants-1997_07
Patent number
US05646232

Reaction notes

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