Methyl iodide → 1-Methylcyclohexane-1-carboxaldehyde

HRID 2377631Notes

Reaction equation

HRID 2377631 reaction equation
[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

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 16275CyclohexanecarboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 111371681-Methylcyclohexane-1-carboxaldehydeYield 83.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3735472570684872b6d3bdb95251a2f7
Source dataset
uspto-grants-2008_12
Patent number
US07470664B2

Reaction notes

Loading…