Hydroquinone → Methyl acrylamidoglycolate methyl ether

HRID 845874Notes

Reaction equation

HRID 845874 reaction equation
[C:1]([NH:5][CH:6]([OH:11])[C:7]([O:9][CH3:10])=[O:8])(=[O:4])[CH:2]=[CH2:3].CO.[CH3:14]OC.C1(C=CC(O)=CC=1)O.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>>[CH3:14][O:11][CH:6]([NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 5

HCID 785HydroquinoneHCID 887MethanolHCID 6049Ethylenediaminetetraacetic AcidHCID 8254Dimethyl EtherHCID 157058Methyl 2-hydroxy-2-(1-oxo-2-propenylamino)acetate

Product 1

HCID 156893Methyl acrylamidoglycolate methyl etherYield 85%

Procedure

Methyl acrylamidoglycolate, as prepared in Example I, in the amount of 100 parts (0.63 mole) is combined with 200 parts of methanol (6.3 moles), 0.10 parts of the methyl ether of hydroquinone and 0.005 part of ethylene-diamine tetraacetic acid and 5.0 parts of a 40% aqueous solution of paratoluenesulfonic acid is added as catalyst. The reaction mixture is heated for 4 hours at reflux temperature and then cooled and filtered. Vacuum stripping of the methanol results in crystallization of the product. An 85% yield of methyl acrylamidoglycolate methyl ether is obtained.

Workup

  1. additionis added as catalyst
  2. temperatureThe reaction mixture is heated for 4 hours
  3. temperatureat reflux temperature
  4. temperaturecooled
  5. filtrationfiltered
  6. customVacuum stripping of the methanol results in crystallization of the product

Sources & evidence

ORD record
ord-63962f70461247b29c2f55b66540cc30
Source dataset
uspto-grants-1988_07
Patent number
US04760168

Reaction notes

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