Butanal → HCID 23450598, compound

HRID 1261745Notes

Reaction equation

HRID 1261745 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.C(OO)(=O)C.[CH:17](=[O:21])[CH2:18][CH2:19]C.OO>C1(C)C=CC=CC=1.C(O)(=O)C.Cl[Cu]>[CH2:17]([O:21][N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][CH:6]([OH:8])[CH2:7][C:2]1([CH3:11])[CH3:1])[CH2:18][CH3:19]

Participants

8

Reactant 4

HCID 261ButanalHCID 784Hydrogen PeroxideHCID 6585Peracetic AcidHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 23450598HCID 23450598, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolventHCID 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. 2.3 g of a 40% solution of peracetic acid in acetic acid are added at 0° C. and the reaction mixture is stirred at room temperature for 3 h. 4.2 ml butanal and 2.4 ml of a 30% aqueous hydrogen peroxide solution are added, followed by 50 mg CuCl after 15 min. The reaction mixture is stirred for 1.5 h at room temperature to give a greenish emulsion. The two phases are separated and the organic one is washed with 10% ascorbic acid solution, water, diluted sodium carbonate sol., diluted sodium chloride sol., and saturated sodium chloride sol. The organic phase is dried over sodium sulfate and finally evaporated to complete dryness under vacuum to afford 1.3 g product.

Workup

  1. stirringThe reaction mixture is stirred for 1.5 h at room temperature
  2. customto give a greenish emulsion
  3. customThe two phases are separated
  4. washthe organic one is washed with 10% ascorbic acid solution, water, diluted sodium carbonate sol., diluted sodium chloride sol., and saturated sodium chloride sol. The organic phase
  5. dry with materialis dried over sodium sulfate
  6. customfinally evaporated

Sources & evidence

ORD record
ord-2836eadc80af42a09fc77cd31a2e6d30
Source dataset
uspto-grants-2013_06
Patent number
US08471031B2

Reaction notes

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