Epichlorohydrin → HCID 23284829, compound

HRID 369005Notes

Reaction equation

HRID 369005 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)[CH3:2].C([CH:12]1[O:14][CH2:13]1)Cl>[OH-].[Na+]>[CH2:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH:13]1[CH2:12][O:14]1)[CH3:2]

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 121013-Ethylphenol

Product 1

HCID 23284829HCID 23284829, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of 3-ethyl phenol (1.50 g, 12.28 mmol) in NaOH (1N) was added epichlorohydrin (2.07 g, 22.47 mmol). The reaction mixture was stirred at room temperature for 4 days. Excess epichlorohydrin was removed by concentration in vacuo and the two-phase mixture treated with NaOH (1N) (10 ml) after addition of THF (10 ml). The reaction mixture was heated to 55° C. for 15 minutes and then stirred at room temperature for 30 minutes. The THF was removed by concentration in vacuo and the product extracted with ethyl acetate (2×50 ml), concentrated in vacuo and purified by flash column chromatography on silica (150:10:1 dichloromethane:methanol:ammonia) to give the product as a yellow oil.

Workup

  1. customExcess epichlorohydrin was removed by concentration in vacuo
  2. additionthe two-phase mixture treated with NaOH (1N) (10 ml)
  3. additionafter addition of THF (10 ml)
  4. temperatureThe reaction mixture was heated to 55° C. for 15 minutes
  5. stirringstirred at room temperature for 30 minutes
  6. customThe THF was removed by concentration in vacuo
  7. extractionthe product extracted with ethyl acetate (2×50 ml)
  8. concentrationconcentrated in vacuo
  9. custompurified by flash column chromatography on silica (150:10:1 dichloromethane:methanol:ammonia)

Sources & evidence

ORD record
ord-0df41a8545ae4363a888ada204ae8ce2
Source dataset
uspto-grants-2000_10
Patent number
US06136824

Reaction notes

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