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

HRID 1195430Notes

Reaction equation

HRID 1195430 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 200 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-19b7f7ff25d64fd9b192c38a982c6496
Source dataset
uspto-grants-1992_05
Patent number
US05110977

Reaction notes

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