Methyl Methacrylate → 2-Methoxyethyl methacrylate

HRID 1764759Notes

Reaction equation

HRID 1764759 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH3:8][O:9][CH2:10]CO.[C-]#N.[K+].COC1C=CC(O)=CC=1.C(OC)(=O)C(C)=C.CO>>[C:1]([O:6][CH2:7][CH2:8][O:9][CH3:10])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 5

HCID 6658Methyl MethacrylateHCID 80192-MethoxyethanolHCID 90154-MethoxyphenolHCID 9032Potassium CyanideHCID 19593510Methyl methacrylate methanol

Product 1

HCID 814662-Methoxyethyl methacrylate

Conditions

Temperature
75 °C

Procedure

400 g of methyl methacrylate (4 mole), 152 g of ethylene glycol monomethyl ether (2 mole), 2.75 g of KCN (0.5%) and 0.14 g of hydroquinone monomethyl ether (250 ppm) are added to a 1 liter round-bottomed flask. The batch is heated to about 75° C. and the methyl methacrylate/methanol-azeotrope is distilled-off by way of a 1 m vigreux column at 65° C. temperature at the head of the column. After 4 hours, the trans-esterification is completed. After cooling of the flask, the sump is filtered to remove the potassium cyanide, and the filter residue is washed with a little methyl methacrylate. The filtrate is concentrated at 40° C. under a water jet vacuum. A residue of ethylene glycol monomethylether methacrylate of 260 g = 90% results.

Workup

  1. customis distilled-off by way of a 1 m vigreux column at 65° C.
  2. temperatureAfter cooling of the flask
  3. filtrationthe sump is filtered
  4. customto remove the potassium cyanide
  5. washthe filter residue is washed with a little methyl methacrylate
  6. concentrationThe filtrate is concentrated at 40° C. under a water jet vacuum

Sources & evidence

ORD record
ord-ea2e9a31817f489faec28d9bcbfd6870
Source dataset
uspto-grants-1978_09
Patent number
US04117238

Reaction notes

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