2,5-Dihydroxybenzoic acid → (2S)-2-methylbutyl 2,5-dihydroxybenzoate

HRID 424307

Reaktionsgleichung

[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CS(O[CH2:17][C@@H:18]([CH3:21])[CH2:19][CH3:20])(=O)=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH2:17][C@@H:18]([CH3:21])[CH2:19][CH3:20])=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 2,5-dihydroxybenzoic acid (15.4 g) in DMF (50 ml) DBU (15.3 ml) was drop wise added. After complete addition (10 min) stirring was continued for 30 min at room temperature, then a solution of (2S)-2-methylbutyl methanesulfonate (16.4 g) in DMF (20 ml) was added drop wise. After complete addition (30 min) the reaction mixture was heated to 80° C. for 6 h. It was then cooled to room temperature, poured into saturated solution of NaHCO3 (200 ml) and extracted with ethyl acetate (2×300 ml). The combined extracts were dried over Na2SO4 and evaporated to dryness. The obtained dark oily residue was purified over silica gel column to give nearly pure (2S)-2-methylbutyl 2,5-dihydroxybenzoate as beige oil.

Aufarbeitung

additionwise added
additionAfter complete addition (10 min)
additionAfter complete addition (30 min) the reaction mixture
temperatureIt was then cooled to room temperature
extractionextracted with ethyl acetate (2×300 ml)
dry with materialThe combined extracts were dried over Na2SO4
customevaporated to dryness
customThe obtained dark oily residue was purified over silica gel column

Quellen und Nachweise

ORD-Eintrag: ord-501a2af4992b46148731bbbee28ad177
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08105662B2

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