Sodium Hydroxide → 4-Methoxy-3-(2-methoxy-ethoxymethyl)-benzoic acid

HRID 1158469Notes

Reaction equation

HRID 1158469 reaction equation
C([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:6]=1)C.[OH-].[Na+]>C1COCC1>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:19])=[O:3])=[CH:6][C:7]=1[CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 686167104-Methoxy-3-(2-methoxy-ethoxymethyl)-benzoic acid ethyl ester

Product 1

HCID 595122624-Methoxy-3-(2-methoxy-ethoxymethyl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-methoxy-3-(2-methoxy-ethoxymethyl)-benzoic acid ethyl ester (0.87 g, 3.24 mmol) in a 1:1 mixture of THF and 4N NaOH (10 mL) is stirred at 50° C. overnight. After cooling, the volatiles are removed at reduced pressure, the remaining aqueous phase is acidified to pH 1 by dropwise addition of HCl 37%, and the resulting suspension is filtered off. The precipitate is washed with water, dried overnight in vacuo to give the title compound. TLC, Rf (hexane/AcOEt 1:1)=0.07. MS: 239.0 [M−H]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 2.71 min. 1H-NMR (DMSO-d6): δ 3.29 (s, 3H), 3.52 (m, 2H), 3.64 (m, 2H), 3.88 (s, 3H), 4.51 (s, 2H), 7.10 (m, 1H), 7.90 (m, 1H), 7.94 (m, 1H), 12.6 (s, br, 1H) ppm.

Workup

  1. temperatureAfter cooling
  2. customthe volatiles are removed at reduced pressure
  3. additionthe remaining aqueous phase is acidified to pH 1 by dropwise addition of HCl 37%
  4. filtrationthe resulting suspension is filtered off
  5. washThe precipitate is washed with water
  6. customdried overnight in vacuo

Sources & evidence

ORD record
ord-94f6d7d78532498bb81013bd7e54186d
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

Loading…