Water → 4-Hydroxy-2-methylpentan-2-yl 2,2-dimethylpropaneperoxoate

HRID 1248559Notes

Reaction equation

HRID 1248559 reaction equation
[OH-].[K+].O.[OH:4][CH:5]([CH3:12])[CH2:6][C:7]([O:10][OH:11])([CH3:9])[CH3:8].[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[C:13]([O:11][O:10][C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:4])[CH3:12])(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium Hydroxide2×HCID 62493Pivaloyl chlorideHCID 157903394-Hydroperoxy-4-methylpentan-2-ol2×

Product 1

HCID 541432174-Hydroxy-2-methylpentan-2-yl 2,2-dimethylpropaneperoxoateYield 81.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A jacketed reactor equipped with a mechanical stirrer, a thermometer and a dropping funnel was charged with 19.9 g (0.160 mole) of 45% KOH, 9.9 g of water, 21.5 g (0.150 mole) of 93.7% 3-hydroxy-1,1-dimethyl butyl hydroperoxide (also known as 4-hydroxy-2-methyl-2-hydroperoxypentane), 25 g of methylene chloride and 0.65 g (0.002 mole) of tetrabutylammonium bromide, a phase transfer catalyst (PTC). The resulting vigorously stirred mixture was cooled to -5° to -2° C. and to it was slowly added 12.6 g (0.100 mole) of 95.4% pivaloyl chloride over a period of about 30 minutes. The resulting product mixture was then stirred for 2 hours at -5° to -2° C. after which 25 g of 10% KOH and an additional 50 g of methylene chloride were added to the reaction mixture. The reaction mass was allowed to separate into two liquid phases at 10° C. and the lower organic layer was removed, dried over about 5% by weight of anhydrous MgSO4 and after the spent desiccant was separated by filtration the methylene chloride was removed in vacuo at 0° to 10° C. Obtained was 24.5 g of liquid product which had an assay of 72.3% according to peroxyester active oxygen content. The corrected yield was 81.3%. An infrared spectrum of the product showed a large broad OH band centered at 3450 to 3550 cm-1.

Workup

  1. customA jacketed reactor equipped with a mechanical stirrer
  2. temperatureThe resulting vigorously stirred mixture was cooled to -5° to -2° C. and to it
  3. customof about 30 minutes
  4. customto separate into two liquid phases at 10° C.
  5. customthe lower organic layer was removed
  6. dry with materialdried over about 5% by weight of anhydrous MgSO4
  7. customafter the spent desiccant was separated by filtration the methylene chloride
  8. customwas removed in vacuo at 0° to 10° C
  9. customObtained

Sources & evidence

ORD record
ord-962d4c832f6740f1af25de21b2a7513a
Source dataset
uspto-grants-1985_06
Patent number
US04525308

Reaction notes

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