Toluene → 1,2,2,6,6-Pentamethyl-4-(oxiran-2-ylmethoxy)piperidine

HRID 1683338Notes

Reaction equation

HRID 1683338 reaction equation
[OH-].[Na+].C1(C)C=CC=CC=1.[OH:10][CH:11]1[CH2:16][C:15]([CH3:18])([CH3:17])[N:14]([CH3:19])[C:13]([CH3:21])([CH3:20])[CH2:12]1.[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:19][N:14]1[C:13]([CH3:21])([CH3:20])[CH2:12][CH:11]([O:10][CH2:22][CH:24]2[O:26][CH2:25]2)[CH2:16][C:15]1([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 1140TolueneHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-

Product 1

HCID 142745051,2,2,6,6-Pentamethyl-4-(oxiran-2-ylmethoxy)piperidine

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

300 g of sodium hydroxide (7.5 mol) are dissolved in 300 ml of water under an argon atmosphere in a 2.5 l sulfonation flask with a mechanical stirrer, condenser and 500 ml dropping funnel. 750 ml of toluene, 48.4 g (0.15 mol) of tetrabutylammonium bromide and 257 g (1.5 mol) of 4-hydroxy-1,2,2,6,6-pentamethylpiperidine are added. 347 g of epichlorohydrin (3.75 mol) are added dropwise at 60° C. in the course of 1.5 hours and the temperature is then kept at 60° C. for a further 4 hours, while stirring. The reaction solution is poured onto 3 l of ice-water and the organic phase is separated off, dried with sodium sulfate and evaporated.

Workup

  1. customthe organic phase is separated off
  2. dry with materialdried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-5ef6ccd3e9114e2a85c46fedee32de06
Source dataset
uspto-grants-1997_06
Patent number
US05637714

Reaction notes

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