Sodium Hydroxide → HCID 67189348, compound

HRID 2366105Notes

Reaction equation

HRID 2366105 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-26a6a390d31848a2b6d1d78aa4d4d49a
Source dataset
uspto-grants-2014_04
Patent number
US08697732B2

Reaction notes

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