Methanol → 1-(2-Phenoxy-ethoxy)-naphthalene-2-carboxylic acid

HRID 1889263Notes

Reaction equation

HRID 1889263 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][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4].[OH-].[Na+].CO>C1COCC1>[O:18]([CH2:17][CH2:16][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])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 688461391-(2-Phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 688427781-(2-Phenoxy-ethoxy)-naphthalene-2-carboxylic acidYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 9.60 g of 1-(2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid methyl ester in 105 ml of THF were added 30 ml of 2 M aqueous sodium hydroxide and 40 ml of methanol. After 3 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 dried over magnesium sulphate, and concentrated and dried in vacuo to yield 7.62 g of 1-(2-phenoxy-ethoxy)-naphthalene-2-carboxylic acid.

Workup

  1. temperatureAfter 3 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. dry with materialThe combined organic layers were dried over magnesium sulphate
  6. concentrationconcentrated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-be8f0d81e2da457cbd43afff41d3ba76
Source dataset
uspto-grants-2013_08
Patent number
US08501981B2

Reaction notes

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