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

HRID 1261750Notes

Reaction equation

HRID 1261750 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.Cl.[CH:15](=[O:17])C>[Cl-].[Na+].[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:15][O:17][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

7

Reactant 4

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 784Hydrogen Peroxide2×HCID 132202,2,6,6-Tetramethyl-4-piperidone

Product 1

HCID 109761931-Methoxy-2,2,6,6-tetramethylpiperidin-4-oneYield 64%

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 5234Sodium ChlorideSolvent

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 1.75 equivalents of hydrogen peroxide in 2M sodium chloride solution, with 1 mol % sodium tungstate added, for 12 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 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 64% of liquid product, crystallizes slowly.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-205d12e2811747b6ae27764c06788ff0
Source dataset
uspto-grants-2013_06
Patent number
US08471031B2

Reaction notes

Loading…