Sodium Dithionite → 2,6-Dimethylhydroquinone

HRID 1631060

Reaktionsgleichung

Reaktionsgleichung von HRID 1631060
[CH3:1][C:2]1[C:3](=[O:10])[C:4]([CH3:9])=[CH:5][C:6](=[O:8])[CH:7]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CCOC(C)=O.O>[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10]

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 682412,6-Dimethyl-1,4-benzoquinone

Produkt 1

HCID 695602,6-DimethylhydroquinoneAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2,6-dimethyl-[1,4]benzoquinone (5 g) and sodium hydrosulfite (10 g) in EtOAc (50 mL) and water (20 mL) was stirred for 30 min. After separation with EtOAc, the organic phase was dried and evaporated to dryness to give a off-white solid 5 g of 2,6-dimethyl-benzene-1,4-diol. The solid was dissolved in dry ether, cooled in an ice-water bath, followed by dropwise addition of sulfuryl chloride (5 g). After stirring the solution at RT for 3 h, workup and purification on silica gel column chromatography (30% EtOAc in hexane) gave 2.2 g 2-chloro-3,5-dimethyl-benzene-1,4-diol.

Aufarbeitung

  1. customAfter separation with EtOAc
  2. customthe organic phase was dried
  3. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f9f984bac65a40f599827533cae5a159
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791155B2

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