Methanol → Methyl 4-(hydroxymethyl)naphthalene-1-carboxylate

HRID 1166737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166737
[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[CH3:16]O>C(OCC)(=O)C.CCCCCC>[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 111064024-Hydroxymethylnaphthoic Acid

Produkt 1

HCID 10878557Methyl 4-(hydroxymethyl)naphthalene-1-carboxylateAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxymethylnaphthoic acid (10 g, 50 mmol), methanol (300 mL), and conc. H2 SO4 (2 mL) was refluxed overnight. The insolubles were filtered off and the filtrate was concentrated. The residue was taken up in ethyl acetate and washed with aqueous NaHCO3 (2×), brine, dried over MgSO4, and concentrated to give a yellow oil. Silica gel column chromatography using ethyl acetate/hexane (1/3) gave the desired product as a yellow oil (3.3 g, 35%).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. filtrationThe insolubles were filtered off
  3. concentrationthe filtrate was concentrated
  4. washwashed with aqueous NaHCO3 (2×), brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-34a6d02e45b1431db20ede61c2f365b4
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613942B1

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