Terephthalic Acid → HCID 11977441, compound

HRID 849265Notes

Reaction equation

HRID 849265 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[CH2:14]([N+:18]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>CO>[C:1]([O-:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=[O:7])=[CH:4][CH:3]=1.[CH2:27]([N+:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:28][CH2:29][CH3:30].[CH2:27]([N+:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 7489Terephthalic AcidHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 11977441HCID 11977441, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Terephthalic acid (0.439 g., 2.64×10-3 mol) (dried in vacuo at 60° C.) partially dissolved in 10 mL of methanol was titrated under an argon atmosphere with 5.3 mL (1.4 g, 5.3×10-3 mol) of tetrabutylammonium hydroxide solution (1 M) in methanol. A fine white precipitate which had formed was removed by centrifugation, washed with methanol, and dried in vacuo, weighed (0.037 g) and discarded. The solvent was removed from the filtrate by rotary vacuum evaporation and the salt residue was dried in vacuo at 60° C. for 18 h to obtain 1.60 g (92%) of product. NMR spectra of the salt were obtained in CDCl3, FIGS. 41 and 42.

Workup

  1. customA fine white precipitate which had formed
  2. customwas removed by centrifugation
  3. washwashed with methanol
  4. customdried in vacuo
  5. customThe solvent was removed from the filtrate by rotary vacuum evaporation
  6. customthe salt residue was dried in vacuo at 60° C. for 18 h

Sources & evidence

ORD record
ord-ecda8b225727458d95063f08883e4568
Source dataset
uspto-grants-2000_01
Patent number
US06011133

Reaction notes

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