3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one oxime → 3-(2,4-Dihydroxyphenyl)-2-cyclohexen-1-one Oxime

HRID 585691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 585691
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:20][CH2:19][CH2:18][C:17](=[N:21][OH:22])[CH:16]=1>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:20][CH2:19][CH2:18][C:17](=[N:21][OH:22])[CH:16]=1

Komponenten

3

Edukt 1

HCID 738836023-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one oxime

Produkt 1

HCID 1363432473-(2,4-Dihydroxyphenyl)-2-cyclohexen-1-one OximeAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one oxime (0.1 g) was heated to 50° C. in methanol (5 ml) containing acidic ion exchange resin (0.3 g). After 4 hr, the mixture was filtered and the resin was washed with ammonia solution (50 ml). Filtrate and washings were combined, evaporated in vacuo and purified by flash column chromatography (SiO2, ethyl acetate/petroleum ether, 3:2, v/v) to furnish the title compound as a yellow solid (0.058 g, 81%). δH (DMSO) (mixture of stereoisomers) 1.68 (2H, m, major), 1.76 (2H, m, minor), 2.26 (2H, m, minor), 2.40-2.54 (4H major+2H minor, overlapping m), 6.15-6.30 (3H major+2H minor, overlapping m), 6.85-6.95 (1H major+2H minor, overlapping m), 9.26 (1H, bs, major), 9.32 (1H, bs, minor), 9.35 (1H, bs, major), 9.40 (1H, bs, minor), 10.17 (1H, s, minor), 10.49(1H, s, major); m/z (ES−) 437 (2M−H)−.

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. washthe resin was washed with ammonia solution (50 ml)
  3. customevaporated in vacuo
  4. custompurified by flash column chromatography (SiO2, ethyl acetate/petroleum ether, 3:2, v/v)

Quellen und Nachweise

ORD-Eintrag
ord-6e38f62918fd4201a8b6dbbfa37fa37c
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933319B2

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