Water → 1,4-Benzenedicarboxylic acid, bis[2-(dimethylamino)ethyl] ester

HRID 1613698Notes

Reaction equation

HRID 1613698 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][OH:17].[OH-:19].[Na+].O>C(Cl)Cl>[C:1]([O:11][CH2:16][CH2:15][N:14]([CH3:18])[CH3:13])(=[O:19])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:17][CH2:16][CH2:15][N:14]([CH3:18])[CH3:13])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7488Terephthaloyl chlorideHCID 79022-(Dimethylamino)ethanolHCID 14798Sodium Hydroxide

Product 1

HCID 108813881,4-Benzenedicarboxylic acid, bis[2-(dimethylamino)ethyl] ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 40.60 g (0.20 mol) of terephthaloyl chloride in 20 ml methylene chloride was gradually added to a solution of 35.66 g (0.40 mol) of 2-dimethylaminoethanol, 16.0 g (0.40 mol) of sodium hydroxide and 200 ml of water and stirred rapidly. The reaction was exothermic and achieved reflux. The mixture was stirred for another 1.75 hours after which the organic layer was separated, washed with water, dried over MgSO4 and concentrated to an oil.

Workup

  1. temperatureachieved reflux
  2. stirringThe mixture was stirred for another 1.75 hours after which the organic layer
  3. customwas separated
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-846478e965284930a0de36a0ca1a48d3
Source dataset
uspto-grants-1993_03
Patent number
US05194472

Reaction notes

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