Terephthaloyl chloride → 1,4-Benzenedicarboxylic acid, 1,4-bis(2-phenoxyethyl) ester

HRID 2363902Notes

Reaction equation

HRID 2363902 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.[O:13]([CH2:20][CH2:21][OH:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(N(CC)CC)C>[O:13]([CH2:20][CH2:21][O:22][C:1](=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:22][CH2:21][CH2:20][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:7])=[CH:4][CH:3]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7488Terephthaloyl chloride2×HCID 31236Phenoxyethanol

Product 1

HCID 77753791,4-Benzenedicarboxylic acid, 1,4-bis(2-phenoxyethyl) ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a typical laboratory setting, bis(aryloxyalkyl)terephthalates are made by reacting terephthaloyl chloride with the corresponding aryloxyalkanol. For example, the reaction of terephthaloyl chloride with 2-phenoxyethanol in the presence of excess triethylamine and a solvent, followed by an organic workup to remove the ammonium salt, concentration, and recrystallization provides bis(2-phenoxyethyl)-terephthalate (see Scheme 1, compound 2 and Synthetic Examples 1 and 2 in U.S. Pat. Appl. Publ. No. 2009/0087764). Unfortunately, the lab procedure is impractical on a commercial scale because of the cost of terephthaloyl chloride and, among other issues, the need to recover a solvent and dispose of the ammonium salt.

Workup

  1. customto remove
  2. concentrationthe ammonium salt, concentration, and recrystallization

Sources & evidence

ORD record
ord-bbe8bdeaf0554ab791f37d3ff0d9dd26
Source dataset
uspto-grants-2014_04
Patent number
US08692013B2

Reaction notes

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