Sodium Hydroxide → HCID 67189348, compound

HRID 1924810Notes

Reaction equation

HRID 1924810 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([CH:8]=O)[C:5](=[O:10])[CH2:4][CH2:3]1.C(Cl)(=O)C([Cl:15])=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:15][CH:8]=[C:6]1[CH2:7][C:2]([CH3:11])([CH3:1])[CH2:3][CH2:4][C:5]1=[O:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 12723855HCID 12723855, compound

Product 1

HCID 67189348HCID 67189348, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5,5-dimethyl-2-oxo-cyclohexanecarbaldehyde (51 g, 331 mmol) in chloroform (250 mL), oxalyl chloride (40 mL, 465 mmol) is rapidly added. After stirring for 3-4 min ice followed by 2 N aq. NaOH (100 mL) is added. The organic phase is separated and the aq. phase is extracted once more with chloroform. The combined organic extracts are washed with water and dried over Na2SO4. The solvent is removed in vacuo to give 2-chloromethylene-4,4-dimethyl-cyclohexanone (50 g) as a brown oil; LC-MS: tR=0.96 min.

Workup

  1. additionis added
  2. customThe organic phase is separated
  3. extractionthe aq. phase is extracted once more with chloroform
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over Na2SO4
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-54a83c8b1632441fa257933f2a412471
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

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