Acetaldehyde → 1-Methoxy-2,2,6,6-tetramethylpiperidin-4-one

HRID 1261749Notes

Reaction equation

HRID 1261749 reaction equation
[CH3:1][C:2]1([CH3:11])[CH2:7][C:6](=[O:8])[CH2:5][C:4]([CH3:10])([CH3:9])[NH:3]1.OO.[C:14](=O)([O-])[O-:15].[Na+].[Na+].Cl.C(=O)C.[Cl-].[Na+]>O>[CH3:14][O:15][N:3]1[C:4]([CH3:10])([CH3:9])[CH2:5][C:6](=[O:8])[CH2:7][C:2]1([CH3:11])[CH3:1]

Participants

8

Reactant 6

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 784Hydrogen Peroxide2×HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 132202,2,6,6-Tetramethyl-4-piperidone

Product 1

HCID 109761931-Methoxy-2,2,6,6-tetramethylpiperidin-4-oneYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The intermediate, 1-oxy-2,2,6,6-tetramethyl-piperidin-4-one, can be produced by reacting 2,2,6,6-tetramethyl-piperidin-4-one with 3 equivalents of hydrogen peroxide in excess water, with 10% sodium carbonate added, for 5 h at 50°. When the reaction is complete, the solution is slightly acidified with 2 N hydrochloric acid to pH 5, then 3 equivalents of acetaldehyde and one equivalent of sodium chloride are added, and two equivalents of 30% hydrogen peroxide are added slowly at 50°. The mixture is stirred at 90° for 2 h, and then cooled. The work-up, as above in example E, gives 62% of liquid product, crystallizes slowly.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-e07f4ff4d3e6432ebae7b79de6137ea5
Source dataset
uspto-grants-2013_06
Patent number
US08471031B2

Reaction notes

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