Benzene → 1-Phenylcyclohexylperoxy neodecanoate

HRID 1461587

Reaction equation

HRID 1461587 reaction equation
[OH-:1].[K+].[C:3]1([C:9]2([O:15][OH:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C=CC=CC=1.[C:23](Cl)(=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30]>O>[C:23]([O:33][O:16][O:15][C:9]1([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:1])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 241BenzeneHCID 14797Potassium HydroxideHCID 94502Neodecanoyl chlorideHCID 185715Hydroperoxide, phenylcyclohexyl-

Product 1

HCID 199810531-Phenylcyclohexylperoxy neodecanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

In a four-necked flask of 200 ml provided with a stirrer was charged 33.7 g of an aqueous solution of 30% potassium hydroxide, to which was added a mixture of 22.1 g of 95% 1-phenylcyclohexyl hydroperoxide and 30 g of benzene while the liquid temperature was maintained at 10° C. with stirring. Furthermore, 19.1 g of neodecanoyl chloride was added dropwise over 7 minutes while the liquid temperature was maintained at 15° C. with stirring. After the liquid temperature was raised to 25° C. and the stirring was continued for 2 hours, 40 g of cold water was added and further the stirring was made for 5 minutes. The water phase was separated and washed with an aqueous solution of 40 g of 5% sodium hydroxide and further with water three times. The solution was dried on magnesium sulfate anhydride and benzene was removed off under vacuum to obtain 24.0 g of a desired compound as a light yellow liquid. This compound had an active oxygen amount of 4.20%, a purity of 91% through calculation and a yield of 63 mol %.

Workup

  1. customIn a four-necked flask of 200 ml provided with a stirrer
  2. additionto which was added
  3. temperaturewas maintained at 15° C.
  4. stirringwith stirring
  5. temperatureAfter the liquid temperature was raised to 25° C.
  6. waitfurther the stirring was made for 5 minutes
  7. customThe water phase was separated
  8. washwashed with an aqueous solution of 40 g of 5% sodium hydroxide and further with water three times
  9. dry with materialThe solution was dried on magnesium sulfate anhydride and benzene
  10. customwas removed off under vacuum

Sources & evidence

ORD record
ord-5a22fc10ee5b40fb927d43002cfa8982
Source dataset
uspto-grants-1991_12
Patent number
US05075495

Linked notes

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