Hydrochloric Acid → 6-(2-methoxyethoxymethoxy)-2-naphthoic acid

HRID 969476

Reaction equation

HRID 969476 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]([O:22]C)=[O:21])[CH:14]=[CH:13]2.Cl>O1CCCC1.CO.O>[CH3:3][O:4][CH2:5][CH2:6][O:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]([OH:22])=[O:21])[CH:14]=[CH:13]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12085484Methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate

Product 1

HCID 120854856-(2-methoxyethoxymethoxy)-2-naphthoic acidYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

12.9 g (325 mmol) of sodium hydroxide pellets are added to a solution of 16.9 g (58 mmol) of methyl 6-(2-methoxyethoxymethoxy)naphthalene-2-carboxylate in 200 ml of tetrahydrofuran, 20 ml of methanol and a few drops of water, and the reaction medium is stirred at room temperature for 4 hours. Next, aqueous 1N hydrochloric acid solution is added until pH=2 is obtained, and the reaction medium is extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated under vacuum. The residue obtained is washed with heptane and filtered. 14.9 g of 6-(2-methoxyethoxymethoxy)-2-naphthoic acid are obtained in the form of a white solid, in a yield of 92%.

Workup

  1. customis obtained
  2. extractionthe reaction medium is extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue obtained
  7. washis washed with heptane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-479e6b9a53a245dea2ec7495b60678ca
Source dataset
uspto-grants-2007_12
Patent number
US07307078B2

Linked notes

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