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Benzoic Acid → 6,8-Di-t-butyl-2-butoxycarbonylchroman

HRID 988840
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 988840
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH:2]=[CH2:3].C(O)(=O)C1C=CC=CC=1.[C:19]([C:23]1[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:26]=[C:25]([CH2:33]OCCCC)[C:24]=1[OH:39])([CH3:22])([CH3:21])[CH3:20]>C(O)CCC>[C:29]([C:27]1[CH:26]=[C:25]2[C:24](=[C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:28]=1)[O:39][CH:2]([C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])[CH2:3][CH2:33]2)([CH3:31])([CH3:32])[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 243Benzoic AcidHCID 8846Butyl AcrylateHCID 99439272,4-di-t-butyl-6-butoxymethyl-1-hydroxybenzene

Produkt 1

HCID 113599626,8-Di-t-butyl-2-butoxycarbonylchromanAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
157.5 °C

Versuchsvorschrift

Butyl acrylate (771.2 g, 6.02 mol) and benzoic acid (12.26 g, 0.10 mol) were added to 2,4-di-t-butyl-6-butoxymethyl-1-hydroxybenzene (665.2 g, net 586.71 g, 2.01 mol) obtained in Example 1, and the mixture was stirred while heating at 150-165° C. for 30 h. 1-Butanol produced by the reaction was removed. After the completion of the reaction, the reaction mixture was quantitatively analyzed by liquid chromatography according to the internal standard method. As a result, 6,8-di-t-butyl-2-butoxycarbonylchroman was obtained in a yield of 87% (1.74 mol). At this time, 6,8-di-t-butyl-3-butoxycarbonylchroman (a position isomer) was produced in about 8%. For use in the next step, excess butyl acrylate was distilled away under reduced pressure, toluene was added to the residue, and benzoic acid was removed with aqueous sodium hydrogen carbonate solution. The 1H-NMR data of the obtained 6,8-di-t-butyl-2-butoxycarbonylchroman are shown below.

Aufarbeitung

  1. customobtained in Example 1
  2. customwas removed
  3. customAfter the completion of the reaction

Quellen und Nachweise

ORD-Eintrag
ord-58ed17b60a5345f48a432d6639dd9ff0
Quelldatensatz
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06635772B2

Notizen zur Reaktion

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