Hydrochloric Acid → HCID 2753389, compound

HRID 703613Notes

Reaction equation

HRID 703613 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[OH:21].[ClH:22]>N1C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[O:21][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:21][C:15]2[CH:16]=[CH:17][C:18]([Cl:22])=[CH:19][C:14]=2[Cl:13])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7488Terephthaloyl chlorideHCID 84492,4-Dichlorophenol

Product 1

HCID 2753389HCID 2753389, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The nitrogen-purged apparatus described in Example 17A for the preparation of DCPSeb was charged with 300 ml of molecular sieves-dried pyridine and 20.3 g of terephthaloyl chloride (0.10 moles, MW=203.0, Aldrich, 97%), which gave a cloudy, yellow mixture. A solution of 32.6 g of 2,4-dichlorophenol (0.20 moles) in 100 ml of dry pyridine was dripped into the stirred mixture over 15 min, causing a 1.3° C. exotherm. The mixture thickened and turned white. It was stirred 6 h more and left unstirred overnight. The mixture was slightly acidified with 10% aq HCl, the crude product isolated from it by vacuum filtration, then rinsed twice with ethanol on the funnel and dried on the funnel to 62 g of slightly wet solid. The product gave a hazy solution in 1200 ml of hot THF, which was filtered hot. After 2 h, a first crop of recystallized solid was isolated by vacuum filtration and rinsed with a minimum of THF. More solids appeared in the filtrate after concentration to 200 ml. A second crop was taken as above after crystallization. The 2 crops were dried on their respective filtration funnels and then overnight at room temperature in a vacuum oven with a slight nitrogen bleed. The combined weight, 27.1 g, was 60% of the theoretical 45.6 g. Elemental analysis is consistent with theory. Calcd. for C20H10O4Cl4 : C, 52.7; H, 2.2; Cl, 31.1. Found: C, 52.8; H. 2.2; Cl, 31.5.

Workup

  1. customThe nitrogen-purged apparatus
  2. customdescribed in Example 17A for the preparation of DCPSeb
  3. customgave a cloudy, yellow mixture
  4. customcausing a 1.3° C.
  5. waitleft unstirred overnight
  6. customthe crude product isolated from it by vacuum filtration
  7. washrinsed twice with ethanol on the funnel
  8. customdried on the funnel to 62 g of slightly wet solid
  9. customThe product gave a hazy solution in 1200 ml of hot THF
  10. filtrationwhich was filtered hot
  11. waitAfter 2 h
  12. customa first crop of recystallized solid was isolated by vacuum filtration
  13. washrinsed with a minimum of THF
  14. concentrationafter concentration to 200 ml
  15. customafter crystallization
  16. customThe 2 crops were dried on their respective filtration funnels
  17. customovernight
  18. customat room temperature

Sources & evidence

ORD record
ord-15fd0a5bb207443798860f5726f9a9ac
Source dataset
uspto-grants-1991_01
Patent number
US04983679

Reaction notes

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