Hydroquinone → Acrylamidoglycolic acid Methyl Ether

HRID 868291Notes

Reaction equation

HRID 868291 reaction equation
[C:1]([NH:5][CH:6]([OH:10])[C:7]([OH:9])=[O:8])(=[O:4])[CH:2]=[CH2:3].[CH3:11]OC(OC)OC.COC.C1(C=CC(O)=CC=1)O>CO>[CH3:11][O:10][CH:6]([NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 8254Dimethyl EtherHCID 9005Trimethyl orthoformateHCID 92230Acetic acid, 2-hydroxy-2-[(1-oxo-2-propen-1-yl)amino]-

Product 1

HCID 19933811Acrylamidoglycolic acid Methyl Ether

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

45 parts of acrylamidoglycolic acid, 90 parts trimethylorthoformate, 0.045 parts of the mono methyl ether of hydroquinone and 35 parts of methanol are mixed in a flask equipped with a stirrer, condensor and thermometer. The mixture was heated at a bath temperature of 60°-65° C. for 24 hours. A small amount of insoluble material was filtered off and discarded. The filtrate was stripped of solvent under vacuum and a rubbery substance was obtained. This material was extracted with ether with stirring for 3 days. The solid which was insoluble in the ether was filtered off and was further extracted with acetone. The acetone was removed to yield 24 g of crude AGME (Mp. 100-102.5).

Workup

  1. customequipped with a stirrer
  2. temperatureThe mixture was heated at a bath temperature of 60°-65° C. for 24 hours
  3. filtrationA small amount of insoluble material was filtered off
  4. customa rubbery substance was obtained
  5. extractionThis material was extracted with ether
  6. filtrationwas filtered off
  7. extractionwas further extracted with acetone
  8. customThe acetone was removed
  9. customto yield 24 g of crude AGME (Mp. 100-102.5)

Sources & evidence

ORD record
ord-3ab54f0a536c4abaac2c3886d17842a7
Source dataset
uspto-grants-1988_10
Patent number
US04778869

Reaction notes

Loading…