Sulfuric Acid → 1,2-Naphthoquinone

HRID 332117

Reaktionsgleichung

Reaktionsgleichung von HRID 332117
[OH:1][C:2]1[C:3](=[O:16])[C:4]2[C:9]([C:10](=O)[C:11]=1CC=C)=[CH:8][CH:7]=[CH:6][CH:5]=2.S(=O)(=O)(O)O>C(O)C>[CH:7]1[CH:8]=[C:9]2[CH:10]=[CH:11][C:2]([C:3](=[O:16])[C:4]2=[CH:5][CH:6]=1)=[O:1]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 178439730HCID 178439730, Verbindung

Produkt 1

HCID 106671,2-Naphthoquinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The process shown in Scheme 2 can be used for the preparation of compounds in Formula II, III and IV when R7 is not hydrogen and X is oxygen from same starting material 1-1 as shown in Scheme 1. The reaction of 2-hydroxy-1,4-naphthoquinone 1-1 with the appropriate allylbromide gives 2-allyloxy-1,4-naphthoquinone 2-2. Rearrangement of 2-2 in ethanol afford 2-hydroxy-3-allyl-1,4-naphthoquinone 2-3, which can be cyclized by sulfuric acid treatment to form orthonaphthoquinone 2-4. Oxidation of 2-4 with n-bromosuccinimide and lead tetraacetate gives 3-acetoxy-orthonaphthoquinone 2-5. Hydrochloric acid treatment of compound 2-5 gives 2-alkyl (or aryl)-3-alkyl (or aryl)-naphtha[2,3-b]furan-4,9-dione 2-6.

Quellen und Nachweise

ORD-Eintrag
ord-570599cd1a4f4732b8eaf7c0292cc618
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877803B2

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