Isopropanol → Tertiary-butylperoxy octadecyl carbonate

HRID 460997Notes

Reaction equation

HRID 460997 reaction equation
[C:1]([O:5][OH:6])([CH3:4])([CH3:3])[CH3:2].Cl[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:9].[OH-].[Na+].C([OH:34])(C)C>CCCCCC>[C:8](=[O:34])([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[O:9][O:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6410tert-Butyl hydroperoxide2×HCID 14798Sodium HydroxideHCID 103922Carbonochloridic acid, octadecyl ester2×

Product 1

HCID 21894194Tertiary-butylperoxy octadecyl carbonate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Tertiary-butylperoxy octadecyl carbonate was prepared by reaction of tertiary-butyl hydroperoxide with octadecyl chloroformate. Tertiary-butyl hydroperoxide, 70 percent (27.0 grams, 0.21 mole) was placed in a flask, and sodium hydroxide, 20 percent (43.3 grams, 0.22 mole) was added slowly at lower than 20° C., followed by the addition of 10.0 grams of isopropanol all at once. Octadecyl chloroformate (66.5 grams, 0.20 mole) and hexane (115.8 grams) were combined in an addition funnel and added over a period of 90 minutes at about 35° C. The resulting mixture wa phase-separated and the organic layer was washed with three 100 milliliter portions of water. Yield was 179.9 grams, 93.2 percent by weight of theoretical.

Workup

  1. additionadded over a period of 90 minutes at about 35° C
  2. customThe resulting mixture wa phase-separated
  3. washthe organic layer was washed with three 100 milliliter portions of water

Sources & evidence

ORD record
ord-f1756452fe3f450eab0e684f01c9aa53
Source dataset
uspto-grants-1977_12
Patent number
US04061704

Reaction notes

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