Diethyl Ether → HCID 14838645, Verbindung

HRID 477485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477485
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][CH:14]=C)[C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].CC[O:18]CC.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O>[C:7]([C:6]1[C:5]([OH:12])=[C:4]([CH2:13][CH:14]=[O:18])[CH:3]=[C:2]([Cl:1])[CH:11]=1)([O:9][CH3:10])=[O:8]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 14838644HCID 14838644, VerbindungHCID 23667635Sodium periodate

Produkt 1

HCID 14838645HCID 14838645, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Osmium tetroxide (1.0 g, 3.9 mmol) was added to a mixture of methyl 5-chloro-2-hydroxy-3-(2-propenyl)benzoate (4c) (22.7 g, 0.1 mol), ether (400 ml), and water (400 ml). After stirring at room temperature for 5 minutes, sodium periodate (47.06 g, 0.22 mol) was added in portions. The mixture was stirred at room temperature for another 21 hours, and then poured into 800 ml of water. The layers were separated and the aqueous layer extracted with ethyl ether (2×400 ml). The organic layers were combined, dried over anhydrous Na2SO4 and then filtered through a column of Florisil (85 g) to remove inorganic impurity. Evaporation of the ether yielded 5c quantitatively as a brown solid, m.p. 49°-59° C., which appeared hygroscopic. The crude product was used for the next reaction without purification. NMR (CDCl3) δ 10.90 (s, 1H, OH), 9.67 (t, 1H, J= 1.5 Hz, CHO), 7.70 (d, 1H, J=3 Hz, aromatic proton), 7.23 (d, 1H, aromatic proton), 3.97 (s, 3H, CH3) and 3.70 (d, 2H, CH2).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for another 21 hours
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ethyl ether (2×400 ml)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered through a column of Florisil (85 g)
  6. customto remove inorganic impurity
  7. customEvaporation of the ether

Quellen und Nachweise

ORD-Eintrag
ord-5eecd8fd536348518dd8ec179c914e84
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04888353

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