Sodium Hydroxide → 3-(Octadecyloxy)-5-(phenylmethoxy)benzoic acid

HRID 1110282Notes

Reaction equation

HRID 1110282 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:5]=1.[OH-].[Na+]>CO.O1CCOCC1>[CH2:19]([O:18][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=1)[C:3]([OH:37])=[O:2])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 540335133-(Octadecyloxy)-5-(phenylmethoxy)benzoic acid methyl ester

Product 1

HCID 193890463-(Octadecyloxy)-5-(phenylmethoxy)benzoic acidYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 46.3 g (0.091 mol) of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid methyl ester and 45 ml (0.27 mol) of 6N NaOH in 750 ml of methanol and 300 ml of dioxane was stirred at reflux for 4 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure. The residue was suspended in water, acidified and filtered to give 44.4 g (99% yield, mp 97°-99°) of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid.

Workup

  1. temperatureat reflux for 4 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reduced pressure
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1fc64a392e864fd7891a26936cab97f8
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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