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

HRID 1757822Notes

Reaction equation

HRID 1757822 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 stirredat 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. customThe solvents were removed at reduced pressure
  2. filtrationThe solid was filtered
  3. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-bc7ef81ef26440e1a6952a117b88d2a7
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

Loading…