Sodium Hydroxide → 2-[2-(Naphthalenyloxy)ethoxy]benzoic acid

HRID 1492835Notes

Reaction equation

HRID 1492835 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH2:12][O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>CO.O1CCOCC1>[C:14]1([O:13][CH2:12][CH2:11][O:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([OH:24])=[O:2])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 570358912-[2-(Naphthalenyloxy) ethoxy]benzoic acid methyl ester

Product 1

HCID 572605232-[2-(Naphthalenyloxy)ethoxy]benzoic acidYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.6 g (3.15 mmol) of 3,5-bis[2-[2-(naphthalenyloxy) ethoxy]benzoic acid methyl ester and 15 mL (15 mmol) of 1N NaOH in 45 mL of methanol and 20 mL of dioxane was stirred at reflux for 2 hours. The usual workup followed by recrystallization from THF-ethyl acetate gave 1.2 g (77% yield, mp 205°-207°) of 3,5-bis[2-[2-(naphthalenyloxy)ethoxy]benzoic acid.

Workup

  1. temperatureat reflux for 2 hours
  2. customThe usual workup followed by recrystallization from THF-ethyl acetate

Sources & evidence

ORD record
ord-5ceefb8a2ffb466682569ac447db433d
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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