Methyl iodide → 1-Methylcyclohexane-1-carboxaldehyde

HRID 1511578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511578
[CH:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9]C(C)([O-])C.[K+].CI>C(Cl)Cl.[Cl-].[Na+].O>[CH3:9][C:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 16275CyclohexanecarboxaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 111371681-Methylcyclohexane-1-carboxaldehydeAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of cyclohexanecarboxaldehyde (10.8 mL, 89.15 mmol) in DCM (500 mL) cooled to 0° C. was added potassium tert-butoxide (13.0 g, 115.9 mmol) and methyl iodide (16.65 mL, 267.5 mmol). After 30 min at this temperature, the mixture was warmed to RT and stirring was continued for an additional 5 h. The reaction was then poured into brine and extracted with DCM. The organic layer was dried over MgSO4 and the solvent was then removed carefully in vacuo to yield 9.4 g (83%) of crude 1-methylcyclohexanecarboxaldehyde which was ˜80% pure and was used directly in the next reaction.

Aufarbeitung

  1. waitwas continued for an additional 5 h
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was then removed carefully in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-21035093e4514c2c861bdb5ef151a64e
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08216999B2

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