Hydrochloric Acid → HCID 178443791, compound

HRID 1448695Notes

Reaction equation

HRID 1448695 reaction equation
Cl.[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:5]=2[N:4]=[N:3]1.[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:12])[C:5]=2[N:4]=[N:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9571-OctanolHCID 178524263HCID 178524263, compound

Product 1

HCID 178443791HCID 178443791, compound

Conditions

Temperature
110 °C

Procedure

n-Octyl alcohol (300 g) was saturated with hydrogen chloride gas passed in subsurface during about 2 hr. while the temperature rose to 55° C. Benzotriazolecarboxylic acid (16.3 g) prepared by the method of Example 1 was added and the reaction mixture was refluxed at 110° C. under reduced pressure for 1.25 hr. during which water was azeotropically distilled and collected in a Dean-Stark trap. Unreacted octyl alcohol was removed by reduced pressure distillation. The residue, which was solid when cooled, was recrystallized from benzene and washed with n-pentane to afford the ester, n-octyl benzotriazolecarboxylate, as a solid mp 64°-65° C. The infrared spectrum was similar to that of the ethyl ester, consistent with the ester structure, and the elemental analysis was as follows:

Workup

  1. customrose to 55° C
  2. additionwas added
  3. distillationduring which water was azeotropically distilled
  4. customcollected in a Dean-Stark trap
  5. customwas removed by reduced pressure distillation
  6. temperaturecooled
  7. customwas recrystallized from benzene
  8. washwashed with n-pentane

Sources & evidence

ORD record
ord-448b27a38f924606bfd7dcaba9e7f8e2
Source dataset
uspto-grants-1980_02
Patent number
US04187186

Reaction notes

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