Glycidol → 3-(4-Nitrophenoxy)propane-1,2-diol

HRID 1112780Notes

Reaction equation

HRID 1112780 reaction equation
[N+:1]([C:4]1(O)[CH:9]=[CH:8][CH:7]=[CH:6][CH2:5]1)([O-:3])=[O:2].[O:11]1[CH2:15][CH:12]1[CH2:13][OH:14].C[O-:17].[Na+]>CO>[OH:11][CH2:15][CH:12]([OH:17])[CH2:13][O:14][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11164GlycidolHCID 10942334Sodium MethoxideHCID 189243361-Nitrophenol

Product 1

HCID 46693343-(4-Nitrophenoxy)propane-1,2-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Nitrophenol (2.6 grams; 19 mmole) is added to a mixture of 2,3-epoxypropanol (1.16 g; 15.6 mmole), anhydrous methanol (10 ml.) and sodium methylate (1.0 g.). After five hours under reflux, the solvent is evaporated and the residue chromatographed on preparative silicic acid plates using chloroform-methanol (9:1) to yield 1,2-dihydroxy-3-(4-nitrophenyloxy)-propane which may be crystallized from chloroform-ethyl acetate. In a similar manner, 1,2-dihydroxy-4-(4-nitrophenyloxy)-butane is prepared.

Workup

  1. temperatureAfter five hours under reflux
  2. customthe solvent is evaporated
  3. customthe residue chromatographed on preparative silicic acid plates

Sources & evidence

ORD record
ord-4102c6aa82034a8b9f509aec05e49ffb
Source dataset
uspto-grants-1978_10
Patent number
US04123614

Reaction notes

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