Triethylamine → 2-Hydroxy-3-pivaloyloxybenzaldehyde

HRID 1739471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739471
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(N(CC)CC)C.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[OH:1][C:2]1[C:9]([O:10][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 905792,3-Dihydroxybenzaldehyde

Produkt 1

HCID 218410482-Hydroxy-3-pivaloyloxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A suspension of 2,3-dihydroxybenzaldehyde (15 g, 109 mmole) in CH2Cl2 (70 ml) was cooled to -10° C. Triethyl amine (5.49 g, 54.3 mmol) was added followed by pivaloyl chloride (6.49 g, 53.9 mmol). The reaction was allowed to stir for 1 hour at -10° C. and then warmed to ambient temperature. The reaction mixture was stirred at ambient temperature overnight, then washed with water, 1N aqueous HCl, saturated aqueous NaHCO3 and water. The organic phase was dried (MgSO4) and evaporated. The residue was purified by chromatography (eluant: ethyl acetate/hexane) to give 2-hydroxy-3-pivaloyloxybenzaldehyde: (10.15 g, 84%).

Aufarbeitung

  1. temperaturewarmed to ambient temperature
  2. stirringThe reaction mixture was stirred at ambient temperature overnight
  3. washwashed with water, 1N aqueous HCl, saturated aqueous NaHCO3 and water
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by chromatography (eluant: ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2ffe3d4f35e94a36bd6789cedee26ef0
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965741

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