Epichlorohydrin → p-(Cyclopropylmethoxy)-phenoxymethyloxirane

HRID 979902Notes

Reaction equation

HRID 979902 reaction equation
[OH-].[Na+].[CH:3]1([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:5][CH2:4]1.[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl>O.C(O)C>[CH:3]1([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH:17]3[CH2:18][O:19]3)=[CH:12][CH:13]=2)[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 137554954-(Cyclopropylmethoxy)phenol

Product 1

HCID 20223083p-(Cyclopropylmethoxy)-phenoxymethyloxirane

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.46 g of sodium hydroxide in 1.8 ml water and 14 ml ethanol, 1.64 g of p-(cyclopropylmethoxy)-phenol and 5.54 g of epichlorohydrin is stirred at room temperature in a nitrogen atmosphere for 24 hours and left at room temperature for 21/2 days. The solvent is evaporated in vacuo and the residue is taken up in ether, washed with water and sodium chloride solution. After drying over anhydrous magnesium sulfate, the solution is filtered and concentrated under reduced pressure to yield p-(cyclopropylmethoxy)-phenoxymethyloxirane which is used directly in the condensation.

Workup

  1. waitleft at room temperature for 21/2 days
  2. customThe solvent is evaporated in vacuo
  3. washwashed with water and sodium chloride solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. filtrationthe solution is filtered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6a8206da3214321ba6eea67393d9053
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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