2,4,4-Trimethyl-1-pentene → HCID 3601441, compound

HRID 463484Notes

Reaction equation

HRID 463484 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:14][C:15]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH2:16]>>[C:15]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1)([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:14]

Participants

4

Reactant 3

HCID 78682,4,4-Trimethyl-1-penteneHCID 6451240Aluminum(III) ChlorideHCID 178418385HCID 178418385, compound

Product 1

HCID 3601441HCID 3601441, compound

Conditions

Temperature
130 °C

Procedure

To benzotriazole (100 g.) melted, heated to 130° C. and stirred there was added aluminum chloride (0.1 g.) and the addition of diisobutylene drop by drop was begun. As the reaction mixture was cooled to 100° C. by refluxing olefin, addition was discontinued until consumption by alkylation allowed the temperature to rise to 120° C. where addition was resumed. This procedure was continued for 11 hrs. during which a total of 90 g. of diisobutylene was added. The reaction mixture was cooled, treated with water, extracted with benzene and filtered to remove solids. The benzene portion was separated, dried and stripped of solvent by rotary evaporation. The product N-tert-octylbenzotriazole was obtained as a tan semi-solid residue.

Workup

  1. temperatureAs the reaction mixture was cooled to 100° C.
  2. temperatureby refluxing
  3. customwas discontinued until consumption by alkylation
  4. customto rise to 120° C.
  5. additionwhere addition
  6. additionof diisobutylene was added
  7. temperatureThe reaction mixture was cooled
  8. additiontreated with water
  9. extractionextracted with benzene
  10. filtrationfiltered
  11. customto remove solids
  12. customThe benzene portion was separated
  13. customdried
  14. customstripped of solvent by rotary evaporation

Sources & evidence

ORD record
ord-f142086eecc44c13ab978f9ebffb67e7
Source dataset
uspto-grants-1985_05
Patent number
US04519928

Reaction notes

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