Ethylene Glycol → 2,6-Dimethoxyphenol

HRID 1701186Notes

Reaction equation

HRID 1701186 reaction equation
C(O)CO.[CH3:5][O:6][C:7]1[C:12]([O:13]C)=[C:11]([O:15][CH3:16])[CH:10]=[C:9](C=O)[CH:8]=1.C([O-])([O-])=O.[K+].[K+].O>C1(C)C=CC=CC=1>[CH3:16][O:15][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([O:6][CH3:5])[C:12]=1[OH:13]

Participants

6

Reactant 4

HCID 174Ethylene Glycol2×HCID 962WaterHCID 68583,4,5-TrimethoxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 70412,6-DimethoxyphenolYield 65.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By way of comparison, a test was carried out with a larger amount of ethylene glycol than that of Example 6. By heating under nitrogen with distillation 212 g (1 mole) of TMBA, 194 g (3 moles) of potash in pellets and 800 ml of ethylene glycol, reaction takes place. The temperature passes from 151° to 190° C. in 1 hour 20; it is held for 2 hours at 190° C. After cooling, dilution with water and neutralization to pH 6, there was obtained, by toluene extraction, 101 g of 2,6-dimethoxy phenol namely a yield of 65.6%. After recrystallization in a water/methanol mixture, with 10% of methanol, the product melted at 54°-55° C. By using a larger amount of ethylene glycol, demethylation and decarboxylation were hence produced.

Workup

  1. waitit is held for 2 hours at 190° C
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-73905542afdf4f5fb45b65ed5c755e61
Source dataset
uspto-grants-1980_03
Patent number
US04191841

Reaction notes

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