Hydroquinone → Butyl (acryloylamino)(butoxy)acetate

HRID 868290Notes

Reaction equation

HRID 868290 reaction equation
[C:1]([NH:5][CH:6]([OH:10])[C:7]([OH:9])=[O:8])(=[O:4])[CH:2]=[CH2:3].S(=O)(=O)(O)O.COC.[C:19]1([CH:26]=[CH:25][C:23](O)=CC=1)O>O.C1(C)C=CC=CC=1.C(O)CCC>[CH2:23]([O:10][CH:6]([NH:5][C:1](=[O:4])[CH:2]=[CH2:3])[C:7]([O:9][CH2:19][CH2:26][CH2:25][CH3:23])=[O:8])[CH2:25][CH2:26][CH3:19]

Participants

8

Reactant 4

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 8254Dimethyl EtherHCID 92230Acetic acid, 2-hydroxy-2-[(1-oxo-2-propen-1-yl)amino]-

Product 1

HCID 57312822Butyl (acryloylamino)(butoxy)acetate

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

One hundred parts of acrylamidoglycolic acid (AGA); 517 parts butanol, 1 part concentrated sulfuric acid and 0.1 part monomethyl ether of hydroquinone were mixed in a flask equipped with a Dean Stark water trap and a stirrer. The mixture was heated until homogeneous. After 5-10 minutes 100 ml of toluene was added and the mixture was brought to reflux and held 5 hours until the theoretical amount of water was collected by azeotrope.

Workup

  1. temperatureThe mixture was heated until homogeneous
  2. temperatureto reflux
  3. customwas collected by azeotrope

Sources & evidence

ORD record
ord-11d9c9df65bf47f8965db450752fdb1c
Source dataset
uspto-grants-1988_10
Patent number
US04778869

Reaction notes

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