Hydrochloric Acid → Cyclohexanecarbaldehyde chlorooxime

HRID 2120087Notes

Reaction equation

HRID 2120087 reaction equation
[CH:1]1([CH:7]=[N:8][OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[ClH:10].OOS([O-])=O.[K+]>CN(C=O)C>[Cl:10][O:9][N:8]=[CH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 638165Cyclohexanecarbaldehyde oximeHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 74053057Cyclohexanecarbaldehyde chlorooxime

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the oxime formed in Example 1 (1 g, 8.25 mmol) in HCl (0.5 M in dioxane; 18.16 ml, 9.08 mmol) and DMF (40 ml) was added oxone (2.79 g, 4.54 mmol) and the resulting mixture was stirred overnight at room temperature. The reaction was partitioned between diethylether and water and the layers were separated. The organic layer was washed with saturated ammonium chloride, dried over sodium sulfate, then concentrates in vacuo using a room temperature water bath. The resulting low boiling liquid was carried on directly to the next step. 1H NMR (CDCl3) δ 1.0-2.2 (m, 10H), 2.35 (m, 1H), 7.8 (bd, 1H).

Workup

  1. customThe reaction was partitioned between diethylether and water
  2. customthe layers were separated
  3. washThe organic layer was washed with saturated ammonium chloride
  4. dry with materialdried over sodium sulfate
  5. customusing a room temperature

Sources & evidence

ORD record
ord-74607d4ea3434f80b7bf5633eb364a01
Source dataset
uspto-grants-2004_02
Patent number
US06689778B2

Reaction notes

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