4-Hydroxybenzaldehyde → p-Octyloxycarbonyloxybenzaldehyde

HRID 648874

Reaktionsgleichung

Reaktionsgleichung von HRID 648874
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Cl[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:12].C1(C)C=CC=CC=1.Cl>N1C=CC=CC=1>[CH2:14]([O:13][C:11]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)=[O:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 1140TolueneHCID 81956Carbonochloridic acid, octyl ester

Produkt 1

HCID 13828007p-OctyloxycarbonyloxybenzaldehydeAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Commercially available p-hydroxybenzaldehyde (50 g) was dissolved in pyridine (400 ml), followed by dropwise adding octyl chloroformate (85 g) under ice cooling, heating on a water bath, allowing the reaction mixture to stand overnight, adding toluene (300 ml) and 6N hydrochloric acid, separating the liquid layer, further washing with an aqueous solution of 2N NaOH, washing with water, drying and distilling off toluene to obtain a raw product of p-octyloxycarbonyloxybenzaldehyde (75 g).

Aufarbeitung

  1. temperatureheating on a water bath
  2. customseparating the liquid layer
  3. washfurther washing with an aqueous solution of 2N NaOH
  4. washwashing with water
  5. customdrying
  6. distillationdistilling off toluene

Quellen und Nachweise

ORD-Eintrag
ord-2540e33eaeda41cbb2db7992398f7311
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04737313

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