Hydroquinone → 4-Methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione

HRID 2051533

Reaktionsgleichung

Reaktionsgleichung von HRID 2051533
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1([CH:15]=C[C:12](O)=[CH:11][CH:10]=1)O.C=C/C=C/C.C=C/C=C\C>C1(C)C=CC=CC=1>[CH3:12][CH:11]1[CH2:10][CH:8]=[CH:15][CH:2]2[C:1]([O:6][C:4](=[O:5])[CH:3]12)=[O:7]

Komponenten

6

Edukt 4

HCID 785HydroquinoneHCID 7923Maleic AnhydrideHCID 622041,3-Pentadiene2×HCID 6437851,3-Pentadiene, (3Z)-

Produkt 1

HCID 127266034-Methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dioneAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Maleic anhydride (68.6 parts) and 70 parts of toluene were introduced into a pressure autoclave, and melted at 55° C. Then, 0.162 part of hydroquinone was added, and 130.9 parts (corresponding to 1.1 moles of trans-1,3-pentadiene per mole of maleic anhydride) of crude trans-1,3-pentadiene composed of 40 % of trans-1,3-pentadiene, 20 % of cis-1,3-pentadiene and 40 % of pentanes was continuously added over 6 hours at 50° C. The temperature was then raised to 60° C., and the reaction was carried out for 3 hours. After the reaction, the reaction mixture was distilled at 90° C. under atmospheric pressure to remove volatile components to give 3-methyltetrahydrophthalic anhydride (melting point 61° C.) in a yield of 99 % as a Diels-Alder reaction product.

Aufarbeitung

  1. additionwas continuously added over 6 hours at 50° C
  2. customAfter the reaction
  3. distillationthe reaction mixture was distilled at 90° C. under atmospheric pressure
  4. customto remove volatile components

Quellen und Nachweise

ORD-Eintrag
ord-61db99f76e62470e820b5e99396eddbf
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05019599

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