Ethanol → HCID 11977441, compound

HRID 1532789Notes

Reaction equation

HRID 1532789 reaction equation
[OH-].[CH2:2]([N+:6]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][CH3:5].[C:19]([OH:30])(=[O:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1.C(O)C>C1C=CC=CC=1>[C:19]([O-:30])(=[O:29])[C:20]1[CH:28]=[CH:27][C:23]([C:24]([O-:26])=[O:25])=[CH:22][CH:21]=1.[CH2:15]([N+:6]([CH2:2][CH2:3][CH2:4][CH3:5])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17][CH3:18].[CH2:15]([N+:6]([CH2:2][CH2:3][CH2:4][CH3:5])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 7489Terephthalic AcidHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 11977441HCID 11977441, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a clean, dry 500 mL round bottom flask equipped with a stir bar, Dean-Starke adapter, condenser, drying tube, and nitrogen inlet, was added 10.0 mL (0.015411 mol) of a 40 wt % aqueous solution of tetrabutylammonium hydroxide, 1.2801 (0.007705 mol) terephthalic acid, 100 mL ethanol, and 150 mL benzene. Lowered apparatus into an oil bath and heated to reflux for 6 hours. The azeotrope distilled at 64.9° C. and the reaction was allowed to remove water overnight. The reaction was cooled to room temperature, and the solvent was removed via rotary evaporation. A sample of the crude product was shown to be very soluble in water, and an NMR was taken which showed the absence of terephthalic acid. The wax-like solid was recrystallized from ethanol/ether to give white crystals, 3.9104 g (78%). Calculated for C40H76N2O4: C, 740219%; H, 11.8019%; N, 4.3161%. Found: C, 69.16; H, 11.74%; N, 4.02%. 1H NMR (CDCl3 300 MHZ): δ 0.92(t 24H), δ 1.30-1.50 (mm 32H), δ 3.10 (t 16H), 6 8.00 (m 4H). Melting point 135-137° C.

Workup

  1. customTo a clean, dry 500 mL round bottom flask
  2. customequipped with a stir bar
  3. customDean-Starke adapter, condenser, drying tube, and nitrogen inlet
  4. temperatureheated
  5. temperatureto reflux for 6 hours
  6. distillationThe azeotrope distilled at 64.9° C.
  7. customto remove water overnight
  8. customthe solvent was removed via rotary evaporation
  9. customThe wax-like solid was recrystallized from ethanol/ether
  10. customto give white crystals, 3.9104 g (78%)

Sources & evidence

ORD record
ord-71d5a80bbc3b46848b01fcb3f9c057f1
Source dataset
uspto-grants-2001_03
Patent number
US06204386B1

Reaction notes

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