Epichlorohydrin → 1,2-Epoxy-3-[3-(2-pyridylmethyl)phenoxy]propane

HRID 1075855Notes

Reaction equation

HRID 1075855 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.[OH-].[Na+]>CO>[O:5]1[CH:3]([CH2:1][O:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([CH2:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][N:6]=3)[CH:14]=2)[CH2:4]1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 215413183-[(Pyridin-2-yl)methyl]phenol

Product 1

HCID 129198521,2-Epoxy-3-[3-(2-pyridylmethyl)phenoxy]propaneYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

19 g of epichlorohydrin is added to a mixture of 18.5 g of 3-(2-pyridylmethyl)phenol, 4.2 g of sodium hydroxide and 200 ml of methanol, and the resulting mixture is stirred at about 50°C for 3 hours. The methanol is then removed, water is added to the residue, and the aqueous solution is extracted with 200 ml of benzene. The benzene layer is washed with 5% sodium hydroxide and with water, and dried over anhydrous magnesium sulfate. The benzene is removed to give 15.0 g of 1,2-epoxy-3-[3-(2-pyridylmethyl)-phenoxy] propane as oil.

Workup

  1. customThe methanol is then removed
  2. additionwater is added to the residue
  3. extractionthe aqueous solution is extracted with 200 ml of benzene
  4. washThe benzene layer is washed with 5% sodium hydroxide and with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe benzene is removed

Sources & evidence

ORD record
ord-96f42c65db9e4ce5a0987d605fb71031
Source dataset
uspto-grants-1976_05
Patent number
US03954776

Reaction notes

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