Sodium Hydroxide → (1-Methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid

HRID 1889267Notes

Reaction equation

HRID 1889267 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:15][CH:16]([CH3:25])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4].[OH-].[Na+]>C1COCC1.CO>[CH3:25][CH:16]([O:15][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:5]=1[C:3]([OH:4])=[O:2])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 688408431-(1-Methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 68842959(1-Methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acidYield 79.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 0.47 g of 1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl ester in 5 ml of THF and 2 ml methanol were added 10 ml of 2 M aqueous sodium hydroxide. After 16 h at room temperature and 2 h at reflux the organic solvents were removed in vacuo. The residue was treated with 2 M hydrochloric acid, and three times extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulphate, concentrated and dried in vacuo to yield 0.36 g of 1-(1-methyl-2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid.

Workup

  1. temperature2 h at reflux the organic solvents
  2. customwere removed in vacuo
  3. additionThe residue was treated with 2 M hydrochloric acid, and three times
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-7e1dea0aa2db4d8fad35800a8c5666b0
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

Loading…