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

HRID 2307153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307153
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-1066a94040bb4009a8f29631dd9a202d
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06828460B2

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