Quinoline → 1,3-Dimethyl-3-(t-butylperoxy)butyl isopropyl carbonate

HRID 65977Notes

Reaction equation

HRID 65977 reaction equation
[CH3:1][CH:2]([OH:13])[CH2:3][C:4]([CH3:12])([O:6][O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:5].N1C2C(=CC=CC=2)C=CC=1.Cl[C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26].Cl.N1C2C(=CC=CC=2)C=CC=1>CCCCC>[C:25](=[O:26])([O:27][CH:28]([CH3:30])[CH3:29])[O:13][CH:2]([CH3:1])[CH2:3][C:4]([CH3:12])([O:6][O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:5]

Participants

6

Reactant 4

HCID 7047Quinoline2×HCID 7917Isopropyl chloroformateHCID 68264Quinoline hydrochlorideHCID 220654633-t-Butylperoxy-1,3-dimethylbutanol

Product 1

HCID 233466141,3-Dimethyl-3-(t-butylperoxy)butyl isopropyl carbonate

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent2×

Procedure

A four-necked 500 ml. round-bottomed flask was equipped with a mechanical stirrer, reflux condenser surmounted by calcium chloride drying tube, addition funnel and thermometer. A solution of 19 g. (0.1 mole) 1,3-dimethyl-3-(t-butylperoxy)butyl alcohol and 13.3 g (slightly over 0.1 mole) quinoline in 250 ml. pentane was placed in the flask which was placed in a water bath at 221/2 ° C. Then 12.3 g (0.1 mole) isopropyl chloroformate was added dropwise over 5 minutes; the temperature did not rise over 23° C. Reaction was not complete after 3 days. Another 3 g. of quinoline was added, and the reaction was completed after another 3 days as indicated by the fact that no further precipitate of quinoline hydrochloride formed when an aliquot of clean pentane solution was withdrawn from the reaction mixture and allowed to stand for 15 minutes. The quinoline hydrochloride was filtered off and washed with 25 ml pentane which was added to the pentane solution. This solution was then successively washed with 25 ml. of 7% hydrochloric acid, two 50 ml. portions of water, and finally dried over sodium sulfate. After removal of drying agent and pentane, a yield of 23.8 g. (86.4%) of material found to be 1,3-dimethyl-3-(t-butylperoxy)butyl isopropyl carbonate by infrared analysis, was obtained.

Workup

  1. customround-bottomed flask was equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. additionsurmounted by calcium chloride drying tube, addition funnel
  4. customwas placed in a water bath at 221
  5. custom2 ° C
  6. customdid not rise over 23° C
  7. customReaction
  8. waitthe reaction was completed after another 3 days
  9. customwas withdrawn from the reaction mixture
  10. waitto stand for 15 minutes
  11. filtrationThe quinoline hydrochloride was filtered off
  12. washwashed with 25 ml pentane which
  13. additionwas added to the pentane solution
  14. washThis solution was then successively washed with 25 ml
  15. dry with materialportions of water, and finally dried over sodium sulfate
  16. customAfter removal
  17. dry with materialof drying agent and pentane
  18. customwas obtained

Sources & evidence

ORD record
ord-fa605c18c67c4c4f80dcb5deb8ca8779
Source dataset
uspto-grants-1978_12
Patent number
US04129700

Reaction notes

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