2,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene)cyclohexanone → Cyclovalone

HRID 714193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 714193
COC[O:4][C:5]1[CH:31]=[CH:30][C:8]([CH:9]=[C:10]2[CH2:15][CH2:14][CH2:13][C:12](=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23]COC)=[C:19]([O:27][CH3:28])[CH:18]=3)[C:11]2=[O:29])=[CH:7][C:6]=1[O:32][CH3:33]>CO.Cl>[OH:23][C:20]1[CH:21]=[CH:22][C:17]([CH:16]=[C:12]2[CH2:13][CH2:14][CH2:15][C:10](=[CH:9][C:8]3[CH:30]=[CH:31][C:5]([OH:4])=[C:6]([O:32][CH3:33])[CH:7]=3)[C:11]2=[O:29])=[CH:18][C:19]=1[O:27][CH3:28]

Komponenten

4

Edukt 1

HCID 695017962,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene)cyclohexanone

Produkt 1

HCID 11366CyclovaloneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

2,6-Bis(4-methoxymethyloxy-3-methoxybenzylidene) cyclohexanone (38j, 0.49 g, 1.1 mmol) was dissolved in methanol (100 ml) and stirred for 15 min at room temperature. Concentrated hydrochloric acid (3 drops) was added and the mixture stirred for 3 hr at 60° C. The methanol was evaporated and the resulting residue extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was recrystallized from ethanol to give 0.26 g (66%) of a yellow solid: mp 177-178° C. [expected mp 179-181° C.]; 1H NMR: δ 1.79 (m, 2H), 2.90 (t, 4H, J=5.4 Hz), 3.89 (s, 6H), 5.88 (s, 2H), 6.91 (s, 2H), 6.96 (d, 2H, J=4.8 Hz), 7.06 (d, 2H, J=8.0 Hz), 7.72 (s, 2H); 13C NMR: δ 23.1, 28.5, 56.0, 113.2, 114.4, 124.4, 128.5, 134.2, 136.9, 146.2, 146.4, 172.8.

Aufarbeitung

  1. stirringthe mixture stirred for 3 hr at 60° C
  2. customThe methanol was evaporated
  3. extractionthe resulting residue extracted into ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a solid
  9. customThe crude solid was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-5535482734a54a599f5616e70189911a
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187397B2

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