O-Xylene → HCID 22961736, compound

HRID 267501Notes

Reaction equation

HRID 267501 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=1[CH3:21]>>[CH3:14][C:15]1[CH:16]=[C:17]([C:2]2[N:4]=[C:5]([C:17]3[CH:18]=[CH:19][C:20]([CH3:21])=[C:15]([CH3:14])[CH:16]=3)[N:7]=[C:8]([C:17]3[CH:18]=[CH:19][C:20]([CH3:21])=[C:15]([CH3:14])[CH:16]=3)[N:1]=2)[CH:18]=[CH:19][C:20]=1[CH3:21]

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 7954Cyanuric chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22961736HCID 22961736, compound

Procedure

A mixture of 36.8 g. (0.20 mole) of cyanuric chloride, 88.0 g. (0.66 mole) of anhydrous aluminum chloride and 250 ml. of o-xylene was heated at 45°C for 1.5 hours. After cooling to room temperature, the mixture was poured into ice water, and then steam distilled to remove the excess o-xylene. The water was decanted from the pot residue and the remaining solid filtered, washed with acetone and dried to yield 58.1 g. of product, m.p. 220°-230°. Recrystallization from benzene gave an analytically pure sample, m.p. 235°-236°.

Workup

  1. additionA mixture of 36.8 g
  2. distillationsteam distilled
  3. customto remove the excess o-xylene
  4. customThe water was decanted from the pot residue
  5. filtrationthe remaining solid filtered
  6. washwashed with acetone
  7. customdried
  8. customto yield 58.1 g
  9. customRecrystallization from benzene
  10. customgave an analytically pure sample, m.p. 235°-236°

Sources & evidence

ORD record
ord-f466e7f3e608468bbec349a29fcb6b95
Source dataset
uspto-grants-1976_03
Patent number
US03943133

Reaction notes

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