Benzene → 2,3-O-Isopropylidene-L-gulonolactone, 2,3-O-Isopropylidene-L-gulono-1,4-lactone, 2,3-O-(1-Methylethylidene)-L-gulonic Acid |A-Lactone, 94840-08-1

HRID 1723485

Reaktionsgleichung

CC1(C)[O:6][CH:5]([CH:7]2[O:12][C:10](=[O:11])[CH:9]3[O:13][C:14]([CH3:17])([CH3:16])[O:15][CH:8]23)[CH2:4][O:3]1.C(OCC)(=O)C.CCCCCC.C1C=CC=CC=1.C(OCC)(=O)C.CC(C)=O>C(O)(=O)C.O>[CH3:16][C:14]1([CH3:17])[O:13][CH:9]2[C:10]([O:12][CH:7]([CH:5]([OH:6])[CH2:4][OH:3])[CH:8]2[O:15]1)=[O:11]

Komponenten

Reaktionsbedingungen

Temperatur: 30 °C

Versuchsvorschrift

2,3:5,6-Di-O-isopropylidene-L-gulonolactone (22.89 g, 88.7 mmol) was dissolved in acetic acid/water (7:1, 200 ml) and stirred at 30° C. for 16 h when t.l.c. (ethyl acetate/hexane 1:1) revealed no starting material (Rf 0.5) and one major product (Rf 0.1). The solvent was removed under reduced pressure to give a yellow oil. Trituration with benzene (50 ml) gave a solid which was shaken with ethyl acetate/acetone (1:1, 250 ml). The resulting suspension was filtered and solvents removed under reduced pressure to yield an amorphous yellow solid, which was recrystallized from ethyl acetate to yield 2,3-O-isopropylidene-L-gulonolactone, (14.31 g, 79%) as a white crystalline solid, m.p. 139°-141° C., [α]D20 +76.2° (C, 1 in acetone).

Aufarbeitung

customThe solvent was removed under reduced pressure
customto give a yellow oil
filtrationThe resulting suspension was filtered
customsolvents removed under reduced pressure
customto yield an amorphous yellow solid, which
customwas recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-0c084429bd6843f69c8cd616e1d823cc
Quelldatensatz: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04861892

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