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

HRID 1603208Notes

Reaction equation

HRID 1603208 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

In a 2.5 l sulfonating flask with mechanical stirrer, condenser and 500 ml dropping funnel 300 g (7.5 mol) of sodium hydroxide are dissolved in 300 g of water under an argon atmosphere. 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 (3.75 mol) of epichlorohydrin are added dropwise over the course of 1.5 hours at 60° C., and then the mixture is stirred at the same temperature for 4 hours more. The reaction solution is poured into 3 l of ice-water, and the organic phase is separated off, dried over sodium sulfate and concentrated by evaporation. Distillation is carried out over a Vigreux column at 0.05 torr and the fraction having the boiling point 71 to 72° C. is collected.

Workup

  1. customthe organic phase is separated off
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated by evaporation
  4. distillationDistillation
  5. customis collected

Sources & evidence

ORD record
ord-b7ae922419f24c5da742862bedf9b42a
Source dataset
uspto-grants-1999_11
Patent number
US05986101

Reaction notes

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