1,2,3-Trichlorobenzene → HCID 520638, compound

HRID 1657682Notes

Reaction equation

HRID 1657682 reaction equation
[C:1]([OH:15])(=[O:14])[C:2]1[C:3](=[CH:7][C:8](=[CH:12][CH:13]=1)[C:9]([OH:11])=[O:10])[C:4]([OH:6])=[O:5].P(Cl)(Cl)(Cl)(Cl)Cl.Cl[C:23]1[C:24](Cl)=[C:25](Cl)[CH:26]=[CH:27][CH:28]=1>>[C:1]([O:15][C:2]1[CH:3]=[CH:7][CH:8]=[CH:12][CH:13]=1)(=[O:14])[C:2]1[C:3](=[CH:7][C:8](=[CH:12][CH:13]=1)[C:9]([O:11][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:10])[C:4]([O:6][C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:5]

Participants

4

Reactant 3

HCID 68951,2,3-TrichlorobenzeneHCID 10708Trimellitic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 520638HCID 520638, compound

Conditions

Temperature
60 °C

Procedure

42 grams of commercially available trimellitic acid was mixed with 138 g. of PCl5 in 100 ml. trichlorobenzene. An exothermic reaction was observed. After completion of the reaction, most of the trichlorobenzene was removed by vacuum distillation. The remaining crude acid chloride was added dropwise with stirring to 65 grams of phenol in about 145 ml. of pyridine. The solution was stirred and cooled with an ice bath during the 10 minute addition period, and then stirred one hour without cooling. The mixture was then heated to 60°C. After being allowed to cool to room temperature, the mixture was poured onto ice having 170 ml. of concentrated HCl therein. An offwhite crystalline solid formed. This was collected by filtration, washed with 5-6 portions of water, and air dried. This product (triphenyl trimellitate) weighed 81 grams. Trichlorobenzene was still detectable in the product; it was therefore recrystallized from 275 ml. methyl ethyl ketone. The white, very fine, fibrous crystals were filtered and washed with two portions of cold methyl ethyl ketone. After air-drying overnight, the final yield of triphenyl trimellitate was 49.5 grams (M.p. 156.5°-157.5°C.)

Workup

  1. customAn exothermic reaction
  2. customAfter completion of the reaction
  3. custommost of the trichlorobenzene was removed by vacuum distillation
  4. additionThe remaining crude acid chloride was added dropwise
  5. stirringThe solution was stirred
  6. temperaturecooled with an ice bath during the 10 minute addition period
  7. stirringstirred one hour
  8. temperaturewithout cooling
  9. temperatureto cool to room temperature
  10. additionthe mixture was poured onto ice having 170 ml
  11. customAn offwhite crystalline solid formed
  12. filtrationThis was collected by filtration
  13. washwashed with 5-6 portions of water, and air
  14. customdried
  15. customit was therefore recrystallized from 275 ml
  16. filtrationThe white, very fine, fibrous crystals were filtered
  17. washwashed with two portions of cold methyl ethyl ketone
  18. customAfter air-drying overnight

Sources & evidence

ORD record
ord-e35ced1d3d3f43c985891c6e3a596197
Source dataset
uspto-grants-1976_06
Patent number
US03962190

Reaction notes

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