Hydroquinone → Triethylammonium

HRID 1376673Notes

Reaction equation

HRID 1376673 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C1(C=CC(O)=CC=1)O.C(C(C)=O)C(C)C.[OH:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][C:27](=[O:31])[C:26]1=[O:32]>O>[CH2:24]([NH+:25]([CH2:30][CH3:29])[CH2:26][CH3:27])[CH3:23].[C:1]([O:6][CH2:29][CH2:30][N:25]([CH2:24][CH2:23][OH:22])[C:26](=[O:32])[C:27]([OH:31])=[O:28])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 4093Methacrylic AcidHCID 7909Methyl Isobutyl Ketone2×HCID 4584884-(2-Hydroxyethyl)-2,3-morpholinedione

Product 2

HCID 1385867TriethylammoniumHCID 131720159HCID 131720159, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Next, in a flask equipped with a stirrer, a thermometer, a decanter, a nitrogen gas-inlet tube, and a reflux condenser were placed 50 g (0.58 moles) of methacrylic acid, 0.1 g (0.1% by weight) of hydroquinone, and 200 ml of methyl isobutyl ketone (hereinafter, referred to as MIBK) and to this mixture was added 54 g (0.58 moles) of N-hydroxyethylmorpholine-2,3-dione, which was prepared in a way as above. Then, the mixture was warmed at 120° C. and the reaction continued for 2 hours by removing water being formed during the reaction by the decanter by means of azeotropic distillation. Return of the solution temperature to room temperature followed by removal of MIBK under reduced pressure gave 2-(1-morpholyl-2,3-dione)ethyl methacylate, which was placed with 120 ml of water in a flask and hydrolyzed by adding dropwise 59 g (0.58 moles) of TEA at 25° C. during 10 minutes to obtain a triethylammonium salt of (2-methacryloyloxyethyl)2-hydroxyethyoxamic acid 10. ##STR26## This ammonium salt was completely soluble in water and identified by IR, which showed absorption bands at 1720 cm-1 for an ester, 1610 cm31 1 for a carboxylic acid, and 2400~2800 cm-1 for a triethylammonium salt, an acid value of 169 (calcd. 162), and a molecular weight of 332.

Workup

  1. customNext, in a flask equipped with a stirrer
  2. customwas prepared in a way as above
  3. customby removing water being
  4. customformed during the reaction by the decanter by means of azeotropic distillation
  5. customReturn of the solution temperature to room temperature followed by removal of MIBK under reduced pressure
  6. customgave 2-(1-morpholyl-2,3-dione)ethyl methacylate, which

Sources & evidence

ORD record
ord-9bbdc26d64e6472aabec07ecf19af1de
Source dataset
uspto-grants-1997_09
Patent number
US05663262

Reaction notes

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