Hydroquinone → HCID 54481936, compound

HRID 1076443Notes

Reaction equation

HRID 1076443 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].C1(C=CC(O)=CC=1)O.[O:14]1[CH2:19][CH2:18][N:17](CCN)[CH2:16][CH2:15]1.[OH-].[Na+].[C:25](#[N:27])[CH3:26]>O>[NH:17]1[CH2:16][CH2:15][O:14][CH:19]([CH2:26][CH2:25][NH:27][C:1](=[O:4])[CH:2]=[CH2:3])[CH2:18]1

Participants

7

Reactant 5

HCID 785HydroquinoneHCID 6342AcetonitrileHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 4082852-Morpholinoethylamine

Product 1

HCID 54481936HCID 54481936, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 1 liter capacity round bottom flask equipped with a stirrer were put 90.5 g (1.0 mole) of acrylic acid chloride and 250 cc of acetonitrile and, as a polymerization-inhibitor, 0.5 g of hydroquinone, and the contents were cooled to 5°-10°C, and thereafter, 130 g (1.0 mole) of 2-morpholinoethylamine were added dropwise thereto in the course of 3 hours while stirring. Afterwards, the contents were stirred further for 2 hours at 40°-50°C. Next, the temperature of the reaction mixture was reduced to 15°-30°C and a solution of 40 g of sodium hydroxide in 100 cc of water was added thereto and the mixture then was stirred for 30 minutes. After removal of the sodium chloride which separated, 97.0 g (52.7%) of a fraction of 122°-124°C/0.05 mmHg were obtained.

Workup

  1. customIn a 1 liter capacity round bottom flask equipped with a stirrer
  2. temperaturethe contents were cooled to 5°-10°C
  3. stirringAfterwards, the contents were stirred further for 2 hours at 40°-50°C
  4. customwas reduced to 15°-30°C
  5. stirringthe mixture then was stirred for 30 minutes
  6. customAfter removal of the sodium chloride which
  7. customseparated
  8. custom97.0 g (52.7%) of a fraction of 122°-124°C/0.05 mmHg were obtained

Sources & evidence

ORD record
ord-90f57c9cf2854b28a21eb194a8df7186
Source dataset
uspto-grants-1976_05
Patent number
US03957492

Reaction notes

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