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

HRID 488273Notes

Reaction equation

HRID 488273 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-6f48a2f28709480da327d0c51a769222
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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