Sodium Thiosulfate → 1-Phenylcyclohexane-1-carbaldehyde

HRID 1270448

Reaktionsgleichung

Reaktionsgleichung von HRID 1270448
[N-]=[C:2]=[O:3].CC(OI1(OC(C)=O)(OC(C)=O)O[C:15](=O)[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[C:15]1([C:14]2([CH:2]=[O:3])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 24477Sodium ThiosulfateHCID 105034IsocyanateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 149226061-Phenylcyclohexane-1-carbaldehydeAusbeute 150,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To compound 2 (5.0 g, 26.3 mmol) in CH2Cl2 (50 mL) was added 13.4 g (31.6 mmol) of Dess-Martin periodinane. After 2 h, sodium thiosulfate (58 g) followed by sat. NaHCO3 (200 mL) was added. After stirring for 1 h, the reaction mixture was diluted with EtOAc then washed with H2O, brine and dried over anhydrous sodium sulfate. Purification by flash chromatography (3:1, hexane-EtOAc) gave 1-phenyl-cyclohexanecarbaldehyde (4.47 g, 90%) as a colorless oil. Mass Spec [M+H]+=189.1.

Aufarbeitung

  1. additionwas added
  2. washthen washed with H2O, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customPurification by flash chromatography (3:1, hexane-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-66d2f3378244432dbc4e79256408d4f6
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202253B2

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