Hydrochloric Acid → 2,5-Dimethyldiphenylmethane

HRID 2049499Notes

Reaction equation

HRID 2049499 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1>[Fe](Cl)(Cl)Cl>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7503Benzyl Chloride2×HCID 7809P-Xylene2×

Product 1

HCID 1394952,5-Dimethyldiphenylmethane

Reagents, catalysts & solvents 1

HCID 24380Iron chloride (FeCl3)Catalyst

Procedure

63.3 Parts of benzyl chloride at 20° are slowly added during 2 hours to a mixture of 1 part of iron (III) chloride and 531 parts of p-xylene held at a temperature of 115°-120° C. The rate of hydrogen chloride evolution is found to be directly proportional to the rate of benzyl chloride addition. After addition, the mixture is held at 120° C. for 3 hours then filtered to remove insoluble matter, and the unreacted p-xylene (406 parts) removed by atmospheric distillation at 135°-145° C. The residue is distilled under reduced pressure at 2-3 mm Hg and a further fraction of p-xylene (64 parts) is obtained at 30°-40° C. The total recovery of p-xylene is 470 parts (98% recovery). The product, 2,5-dimethyldiphenylmethane is obtained at 126°-134° C.: yield 80 parts (82% of theory). A residue of 10.1 parts of polymer remains after distillation.

Workup

  1. customheld at a temperature of 115°-120° C
  2. additionAfter addition
  3. filtrationthen filtered
  4. customto remove insoluble matter
  5. customthe unreacted p-xylene (406 parts) removed by atmospheric distillation at 135°-145° C
  6. distillationThe residue is distilled under reduced pressure at 2-3 mm Hg
  7. customa further fraction of p-xylene (64 parts) is obtained at 30°-40° C

Sources & evidence

ORD record
ord-a21a7c8790d849a6bd20c52107c64b21
Source dataset
uspto-grants-1980_04
Patent number
US04197417

Reaction notes

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