Sodium Hydroxide → 3-Nitro-5-(octadecyloxy)benzoic acid

HRID 1110262Notes

Reaction equation

HRID 1110262 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[C:8]([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][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[C:6]([N+:29]([O-:31])=[O:30])[CH:5]=1.[OH-].[Na+]>CO.O1CCOCC1>[N+:29]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([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][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=1)[C:3]([OH:32])=[O:2])([O-:31])=[O:30]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 536989543-Nitro-5-(octadecyloxy)benzoic acid methyl ester

Product 1

HCID 193889433-Nitro-5-(octadecyloxy)benzoic acidYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4.5 g of 3-nitro-5-(octadecyloxy)benzoic acid methyl ester and 4 ml of 6N NaOH in 200 ml of methanol and 50 ml of dioxane was stirred at reflux for 2.5 hours. The solvents were removed at reduced pressure and the residue was acidified with 1N HCl. The solid was filtered and recrystallized from methanol-water to give 2.7 g (62% yield, mp 101°-103°) of 3-nitro-5-(octadecyloxy)benzoic acid.

Workup

  1. temperatureat reflux for 2.5 hours
  2. customThe solvents were removed at reduced pressure
  3. filtrationThe solid was filtered
  4. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-07517dfc2237434d891e2f1ecc6f208e
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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