Formaldehyde → 4-Hydroxy-2,3,5-trimethylbenzaldehyde

HRID 85010

Reaktionsgleichung

Reaktionsgleichung von HRID 85010
C1N2CN3CN(C2)CN1C3.C=O.[C:13]([O-])(=[O:15])C.[NH4+].[CH3:18][C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[C:21]([CH3:26])[C:20]=1[OH:27]>C(O)(=O)C>[CH3:25][C:24]1[C:19]([CH3:18])=[C:20]([OH:27])[C:21]([CH3:26])=[CH:22][C:23]=1[CH:13]=[O:15]

Komponenten

6

Edukt 4

HCID 712Formaldehyde2×HCID 4101HexamethylenetetramineHCID 170162,3,6-TrimethylphenolHCID 517165Ammonium Acetate2×

Produkt 1

HCID 108990214-Hydroxy-2,3,5-trimethylbenzaldehydeAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Instead of hexamethylenetetramine as applied in Example 2A and 2B, formaldehyde and ammonium acetate in acetic acid were used for formylation as illustrated below. A 250 ml three neck round bottom flask equipped with a reflux condenser was charged with 20.4 g (0.15 mol) of 2,3,6-trimethylphenol. 100 ml acetic acid, 3.09 g (0.04 mol) of ammonium acetate and 3.243 g (0.04 mol) of formalin solution were added to it. The reaction mass was heated at 120° C. over a period of 2.5 hrs. The completion of reaction was confirmed by TLC. The reaction mass was poured into 400 ml ice cold water with stirring. The solid was filtered and washed with 2×50 ml process water. The product was dried under vacuum to afford 17 g (75%) of crude 2,3,5-trimethyl-4-hydroxy-benzaldehyde. The purification of crude product with 1% sodium hydroxide solution afforded 13 g (53%) of pure 2,3,5-trimethyl-4-hydroxyl-benzaldehyde.

Aufarbeitung

  1. customThe completion of reaction
  2. filtrationThe solid was filtered
  3. washwashed with 2×50 ml process water
  4. customThe product was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-05837208b17746a08c42c30a85c05bfd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846982B2

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