Benzene → HCID 20291559, compound

HRID 2049947Notes

Reaction equation

HRID 2049947 reaction equation
[OH-:1].[Na+].[C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH3:4].[CH:19]1[CH:24]=CC=C[CH:20]=1>>[CH2:20]([O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH3:4])[CH:19]1[O:1][CH2:24]1

Participants

4

Reactant 3

HCID 241BenzeneHCID 14798Sodium HydroxideHCID 123377Phenol, o-(alpha,alpha-dimethylbenzyl)-

Product 1

HCID 20291559HCID 20291559, compound

Procedure

The cumylphenyl glycidyl ether was prepared as follows: a 3-liter flask equipped with a mechanical stirrer, thermometer, addition funnel, and external heating and cooling devices was charged sequentially with 1 liter of benzene, 1 liter of 4.5 wt. % aqueous sodium hydroxide and 1 mole of cumylphenol. The cumylphenol salt dispersion formed after mixing was cooled to 10°-15° C., mixed and maintained at 10°-15° C. during the addition of 1.1 moles of epichlorohydrin over a four hour period. After the addition of the chlorohydrin, the reaction mix was warmed to 50° C. for 8 hours. The two phases which formed were separated and the water phase discarded. The organic phase was thrice washed with cold water and the residual organic material fractionated. One hundred ninety grams (71 mole %) of a pale yellow oil having a boiling point at 5 mm Hg of 258°-263° C. was obtained. The oil had an Epoxide Number determined by MgCl2 -HCl titration of 3.72 meq/g, while the theoretical Epoxide Number for cumylphenol glycidyl ether is 3.73 meq/g.

Workup

  1. customThe cumylphenyl glycidyl ether was prepared
  2. customa 3-liter flask equipped with a mechanical stirrer
  3. additionthermometer, addition funnel
  4. temperatureexternal heating
  5. temperaturecooling devices

Sources & evidence

ORD record
ord-96e27f778379408d9f3d3222ad083513
Source dataset
uspto-grants-1980_04
Patent number
US04199517

Reaction notes

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