tert-Butyl hydroperoxide → HCID 14268088, compound

HRID 2107358Notes

Reaction equation

HRID 2107358 reaction equation
[OH-].[K+].[C:3]([O:7][OH:8])([CH3:6])([CH3:5])[CH3:4].[CH2:9](Cl)/[CH:10]=[C:11](/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])\[CH3:12]>S1(CCCC1)(=O)=O>[C:3]([O:7][O:8][CH2:9]/[CH:10]=[C:11](/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])\[CH3:12])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 14797Potassium HydroxideHCID 6372219Geranyl chloride

Product 1

HCID 14268088HCID 14268088, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
10 °C

Procedure

Sulpholane (40 cc) and potassium hydroxide pellets (6.5 g) are introduced into a 250-cc three-necked round-bottomed flask. After cooling to 10° C., a 70% strength aqueous solution of tert-butyl hydroperoxide (12.9 g) is added dropwise. The temperature is maintained at 20° C. for two hours and geranyl chloride (17.2 g, 0.1 mole) is then added dropwise at a temperature of between 10° and 20° C. The solution is kept at 20° C. for 16 hours. After extraction with pentane and purification of the product obtained by flash chromatography, geranyl tert-butyl peroxide (12 g) is obtained, and its structure is confirmed by the infrared spectrum, the mass spectrum and the proton nuclear magnetic resonance spectrum.

Workup

  1. temperatureThe temperature is maintained at 20° C. for two hours
  2. extractionAfter extraction
  3. customwith pentane and purification of the product
  4. customobtained by flash chromatography

Sources & evidence

ORD record
ord-9f5a79acdf4d45699117f8d943dc6cda
Source dataset
uspto-grants-1990_06
Patent number
US04933501

Reaction notes

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