Sodium Hydroxide → 3,4-Bis(tetradecyloxy)benzoic acid

HRID 488279Notes

Reaction equation

HRID 488279 reaction equation
C[O:2][C:3](=[O:40])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:6]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:5]=1.[OH-].[Na+]>CO.O1CCOCC1>[CH2:26]([O:25][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:3]([OH:40])=[O:2])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 120485573,4-Bis(tetradecyloxy)benzoic acid methyl ester

Product 1

HCID 190162583,4-Bis(tetradecyloxy)benzoic acidYield 73.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3,4-bis(tetradecyloxy)benzoic acid methyl ester (1.1 g, 2.0 mmol) and 1.6 ml (9.6 mmol) of 6N NaOH in 40 ml of methanol and 20 ml of dioxane was stirred at reflux for 17 hours. The solvents were removed at reduced pressure, the residue was acidified and the solid was filtered and recrystallized from methanol-THF-water to give 0.8 g (73% yield, mp 112°-113°) of 3,4-bis(tetradecyloxy)benzoic acid.

Workup

  1. temperatureat reflux for 17 hours
  2. customThe solvents were removed at reduced pressure
  3. filtrationthe solid was filtered
  4. customrecrystallized from methanol-THF-water

Sources & evidence

ORD record
ord-e56c65918aec4bc69d906b45b9df40bb
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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