Methanol → Methyl 4-methylnaphthalene-1-carboxylate

HRID 1610208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610208
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:19]O>>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:19])=[O:13])=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 30142854-Methyl-1-naphthalenecarboxylic acid

Produkt 1

HCID 21973653Methyl 4-methylnaphthalene-1-carboxylateAusbeute 97 %

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 4-methyl-1-naphthalenecarboxylic acid (4.14 g, 22.2 mmol) in methanol (50 ml) was added thionyl chloride (3 ml), and the mixture was stirred at 60° C. overnight. The reaction solution was concentrated, water (100 ml) was added and the mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced ressure to give methyl 4-methyl-1-naphthalenecarboxylate (4.32 g, 97%) as a colorless oil.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated
  2. additionwater (100 ml) was added
  3. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
  4. washThe extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced ressure

Quellen und Nachweise

ORD-Eintrag
ord-7da5ef1b3ee84ce58efb74d553855d9d
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06982348B2

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