Epichlorohydrin → 2-{4-[(Oxiran-2-yl)methoxy]phenyl}ethan-1-ol

HRID 845879Notes

Reaction equation

HRID 845879 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([CH:19]1[O:21][CH2:20]1)Cl>C(#N)C>[OH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([O:1][CH2:17][CH:19]2[O:21][CH2:20]2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 104201452-{4-[(Oxiran-2-yl)methoxy]phenyl}ethan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

30.0 g p-hydroxyphenethyl alcohol, 60 g of anhydrous potassium carbonate and 50.28 g of epichlorohydrin were refluxed in 250 mL of acetonitrile for 5 hrs. After cooling, filtering and removing acetonitrile at reduced pressure, 300 mL of toluene were added and the toluene removed under reduced pressure. The residual oil solidifies on standing and is used directly in the next step. Yield=43.2 g, c. 100% yield. This solid after recrystallization in water has a melting point of 56°-58.5° C.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltering
  3. customremoving acetonitrile at reduced pressure, 300 mL of toluene
  4. additionwere added
  5. customthe toluene removed under reduced pressure
  6. customThis solid after recrystallization in water

Sources & evidence

ORD record
ord-694244c85d274fb2bf65622836be79be
Source dataset
uspto-grants-1988_07
Patent number
US04760182

Reaction notes

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