Ethanol → 1,2-Epoxy-3-(2-propylphenoxy)propane

HRID 2163395Notes

Reaction equation

HRID 2163395 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH2:2][CH3:3].Cl[CH2:12][CH:13]1[O:15][CH2:14]1.C(O)C.[OH-].[K+]>O>[O:15]1[CH:13]([CH2:12][O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:1][CH2:2][CH3:3])[CH2:14]1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 7835EpichlorohydrinHCID 125702-PropylphenolHCID 14797Potassium Hydroxide

Product 1

HCID 123558511,2-Epoxy-3-(2-propylphenoxy)propane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 27.2 parts of 2-propylphenol and 56 parts of 1-chloro-2,3-epoxypropane in 30 parts of ethyl alcohol, heated under reflux, was added a solution of 13.2 parts of potassium hydroxide in 50 parts of ethyl alcohol and 6 parts of water over 15 minutes and the mixture obtained was heated under reflux for a further 2 hours. The mixture was poured into 1,000 parts of water and extracted with ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulphate, filtered and evaporated to yield a yellow oil. The oil was distilled at the water pump to yield 31.0 parts of 1,2-epoxy-3-(2-propylphenoxy)propane, boiling point 155°-158° at 15 mm.

Workup

  1. temperatureunder reflux
  2. customthe mixture obtained
  3. temperaturewas heated
  4. temperatureunder reflux for a further 2 hours
  5. extractionextracted with ethyl acetate
  6. customThe organic phase was separated
  7. washwashed with water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customto yield a yellow oil
  12. distillationThe oil was distilled at the water pump

Sources & evidence

ORD record
ord-1513bde8ee2248f2b9644cfbc7e1f6d9
Source dataset
uspto-grants-1979_01
Patent number
US04133889

Reaction notes

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