Guaiacol → ((o-Methoxyphenoxy)methyl)oxirane

HRID 1285540Notes

Reaction equation

HRID 1285540 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].O1[CH2:15][CH2:14][O:13][CH2:12]C1.[OH-].[Na+].C(C1OC1)Cl>O.CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:15][CH:14]1[O:13][CH2:12]1

Participants

7

Reactant 4

HCID 460GuaiacolHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 312751,4-Dioxane

Product 1

HCID 98357((o-Methoxyphenoxy)methyl)oxirane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 2-methoxyphenol(76 g) dissolved in about 60 ml of water and 200 ml of dioxane containing 29 g of sodium hydroxide is slowly added a large excess of epichlorohydrin (80 g). The solution is stirred at reflux temperature for 3 hrs. The mixture is diluted with ether, washed with two portions of water and dried using anhydrous magnesium sulfate. Evaporation of the dried extract, followed by distillation of the residue produced the product, 1-(2-methoxyphenoxy)-2,3-epoxypropane.

Workup

  1. temperatureat reflux temperature for 3 hrs
  2. washwashed with two portions of water
  3. customdried
  4. customEvaporation of the dried
  5. extractionextract
  6. distillationfollowed by distillation of the residue

Sources & evidence

ORD record
ord-7a3f57f84180491c8f1da4510f1a000c
Source dataset
uspto-grants-1986_01
Patent number
US04567264

Reaction notes

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