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

HRID 2073701

Reaktionsgleichung

Reaktionsgleichung von HRID 2073701
[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

Versuchsvorschrift

Maleic anhydride (68.6 parts) and 70 parts of toluene were fed into an autoclave, and melted at 55° C. Then, 0.162 part of hydroquinone was added. Subsequently, 30.9 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 elevated to 60° C. and the reaction was carried out for 3 hours. After the reaction, the volatile components were removed by distillation at 90° C. under atmospheric pressure. As the Diels-Alder reaction product, 3-methyltetrahydrophthalic anhydride (melting point 61° C.) was obtained in a yield of 99%.

Aufarbeitung

  1. additionwas continuously added over 6 hours at 50° C
  2. customwas then elevated to 60° C.
  3. customAfter the reaction
  4. customthe volatile components were removed by distillation at 90° C. under atmospheric pressure
  5. customAs the Diels-Alder reaction product

Quellen und Nachweise

ORD-Eintrag
ord-4e099701de104f4db08dac3056907240
Quelldatensatz
uspto-grants-1990_04
Patentnummer
US04919925

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