Glycidol → 3-[4-(2-Methoxyethyl)phenoxy]-

HRID 2350946Notes

Reaction equation

HRID 2350946 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[O:12]1[CH2:16][CH:13]1[CH2:14][OH:15]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:16][CH:13]([OH:12])[CH2:14][OH:15])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 11164GlycidolHCID 925164-(2-Methoxyethyl)phenol

Product 1

HCID 131868493-[4-(2-Methoxyethyl)phenoxy]-Yield 86.2%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6212ChloroformSolvent

Procedure

39 g of 4-(2-methoxy-ethyl)-phenol are heated to about 120° C., after addition of 0.5 g of benzyl-tributylammonium chloride, and 20.4 g of 2,3-epoxypropanol are added dropwise in the course of 15 minutes. The mixture is allowed to cool, the syrup is dissolved in CHCl3, the solution is washed with water and the CHCl3 residue is purified by preparative HPLC. 50 g of 3-[4-(2-methoxyethyl)-phenoxy]-propane-1,2-diol are obtained.

Workup

  1. additionare added dropwise in the course of 15 minutes
  2. temperatureto cool
  3. washthe solution is washed with water
  4. customthe CHCl3 residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-7948724dbfb34d3dbab40b4e88f1a9ce
Source dataset
uspto-grants-1989_10
Patent number
US04871775

Reaction notes

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