Water → HCID 20535823, compound

HRID 1156274Notes

Reaction equation

HRID 1156274 reaction equation
[OH2:1].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11].[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:15]([O:1][O:14][C:6]1[CH:7]=[C:8]([O:12][CH3:13])[C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=1)[CH:17]1[O:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 695053,4,5-Trimethoxyphenol

Product 1

HCID 20535823HCID 20535823, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a suitable reaction vessel fitted with an attachment for the azeotropic separation of water, 18.4 g (0.1 mole) of 3,4,5-trimethoxyphenol are brought to the boil with 37 g (0.4 mole) of epichlorohydrin, followed by the dropwise addition over a period of 30 minutes of 10 g (0.1 mole) of 40% sodium hydroxide, the water being simultaneously removed azeotropically from the circuit. After the sodium hydroxide has been added, the mixture is left to react for 1 hour at boiling temperature, subsequently diluted with approximately 100 ml of toluene and the NaCl precipitated is filtered off. The filtrate is fractionated first under normal pressure and then in vacuo. The 3,4,5-trimethoxyphenoxy glycidyl ether is obtained as a colorless oil at b.p.1.0 =175°-180° C. Yield 19.2 g, corresponding to 80% of the theoretical, based on trimethoxyphenol.

Workup

  1. customthe water being simultaneously removed azeotropically from the circuit
  2. additionAfter the sodium hydroxide has been added
  3. waitthe mixture is left
  4. customto react for 1 hour
  5. customthe NaCl precipitated
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-4457789153fe4d688a0f788a42e59aaa
Source dataset
uspto-grants-1982_06
Patent number
US04335126

Reaction notes

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