3-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester → 3-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid

HRID 1690470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690470
C[O:2][C:3](=[O:22])[C:4]1[C:5](=[C:10]([O:14][CH2:15][C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8]C)=[O:7]>[OH-].[Na+]>[Cl:21][C:18]1[S:17][C:16]([CH2:15][O:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:4]([C:3]([OH:22])=[O:2])[C:5]=2[C:6]([OH:8])=[O:7])=[CH:20][CH:19]=1

Komponenten

3

Edukt 1

HCID 669061873-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester

Produkt 1

HCID 669067303-(5-Chloro-thiophen-2-ylmethoxy)-phthalic acidAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 3-(5-chloro-thiophen-2-ylmethoxy)-phthalic acid dimethyl ester (2.3 g, 6.7 mmol) in reagent alcohol (100 mL) and 3 N sodium hydroxide (60 mL) was refluxed for two hours. The solution was evaporated and the residue was dissolved in water (100 mL) and washed with methylene chloride (3×100 mL) then acidified to pH around 4. The resulting mixture was extracted with ethyl acetate (2×100 mL) and the combined organic layers was washed with water (2×100 mL), dried and concentrated to give 3-(5-chloro-thiophen-2-ylmethoxy)-phthalic acid as an off-white solid (1.6 g, 76% yield). The product was used in the next step without further purification.

Aufarbeitung

  1. customThe solution was evaporated
  2. dissolutionthe residue was dissolved in water (100 mL)
  3. washwashed with methylene chloride (3×100 mL)
  4. extractionThe resulting mixture was extracted with ethyl acetate (2×100 mL)
  5. washthe combined organic layers was washed with water (2×100 mL)
  6. customdried
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0065bc287032480a98a624454989e9bd
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153659B2

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