Acetone → 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

HRID 1606412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1606412
[OH-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]=1[OH:15])[CH:10]=[O:11])([CH3:6])([CH3:5])[CH3:4].[CH3:20][C:21]([CH3:23])=[O:22].Cl>C(O)C.O>[CH3:20][C:21]([CH:23]=[CH:10][C:9]1[CH:8]=[C:7]([C:3]([CH3:4])([CH3:6])[CH3:5])[C:14]([OH:15])=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:12]=1)=[O:22].[C:16]([C:13]1[CH:12]=[C:9]([CH:8]=[C:7]([C:3]([CH3:6])([CH3:5])[CH3:4])[C:14]=1[OH:15])[CH:10]=[O:11])([CH3:19])([CH3:18])[CH3:17]

Komponenten

8

Edukt 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehyde

Produkt 2

HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeAusbeute 94 %HCID 215849HCID 215849, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

3,5-di tert.butyl-4-hydroxystyryl methyl ketone was prepared by adding a solution of 8 grams of sodium hydroxide in 100 milliliters of absolute ethanol to a mixture of 23.4 grams of 3,5-di tert.butyl-4-hydroxybenzaldehyde and 58 grams of acetone. The reaction mixture was stirred at room temperature for 14 hours and then at reflux temperature for 71/2 hours. After cooling, it was poured into 500 milliliters of water and the resulting mixture was neutralized by the addition of dilute hydrochloric acid. The sticky solid which precipitated was filtered off and mixed with petroleum ether. Filtration yielded 11 grams of unreacted 3,5-di tert.butyl-4-hydroxybenzaldehyde. From the filtrate was isolated 5.5 grams of the desired product which melted at 101° to 105° C.

Aufarbeitung

  1. temperatureat reflux temperature for 71/2 hours
  2. temperatureAfter cooling
  3. customThe sticky solid which precipitated
  4. filtrationwas filtered off
  5. additionmixed with petroleum ether
  6. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-dcc0dc544a45492ea6d918666d20bfac
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03953398

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