Acetic Acid → HCID 23450598, compound

HRID 1261746Notes

Reaction equation

HRID 1261746 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][CH:6]([OH:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.OO.C(O)(=O)C.[CH:18](=[O:22])[CH2:19][CH2:20]C>C1(C)C=CC=CC=1.Cl[Cu]>[CH2:18]([O:22][N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH2:7][C:2]1([CH3:11])[CH3:1])[CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 261ButanalHCID 784Hydrogen PeroxideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 23450598HCID 23450598, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1140TolueneSolvent

Procedure

1.8 g 2,2,6,6-tetramethyl-piperidin-4-ol (intermediate product of Ciba Specialty Chemicals Inc.) are suspended in 7 ml of toluene. 3.6 ml of a 30% aqueous hydrogen peroxide solution and 0.41 g acetic acid are added at 5° C. and the solution is stirred at room temperature over night. 4.2 ml butanal and, after 15 min., 50 mg CuCl are added. The reaction mixture is stirred for 18 h at room temperature. The two phases are separated and the organic one is washed with 0.05M hydrochloric acid, sodium bisulfite solution, water, diluted sodium hydroxide solution, water and finally saturated sodium chloride solution. The organic phase is dried over sodium sulfate and finally evaporated to complete dryness under vacuum to afford 0.38 g product.

Workup

  1. stirringThe reaction mixture is stirred for 18 h at room temperature
  2. customThe two phases are separated
  3. washthe organic one is washed with 0.05M hydrochloric acid, sodium bisulfite solution, water, diluted sodium hydroxide solution, water and finally saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customfinally evaporated

Sources & evidence

ORD record
ord-631e4ad7df844a0ab26e16e0a957be37
Source dataset
uspto-grants-2013_06
Patent number
US08471031B2

Reaction notes

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