Toluene → 2,2,6,6-Tetramethyl-4-[(oxiran-2-yl)methoxy]piperidine

HRID 1603207Notes

Reaction equation

HRID 1603207 reaction equation
[OH-].[Na+].C1(C)C=CC=CC=1.[OH:10][CH:11]1[CH2:16][C:15]([CH3:18])([CH3:17])[NH:14][C:13]([CH3:20])([CH3:19])[CH2:12]1.[CH2:21]([CH:23]1[O:25][CH2:24]1)Cl>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:17][C:15]1([CH3:18])[CH2:16][CH:11]([O:10][CH2:21][CH:23]2[O:25][CH2:24]2)[CH2:12][C:13]([CH3:20])([CH3:19])[NH:14]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 142745062,2,6,6-Tetramethyl-4-[(oxiran-2-yl)methoxy]piperidine

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In a 750 ml sulfonating flask with mechanical stirrer, condenser and 100 ml dropping funnel 64.0 g (1.6 mol) of sodium hydroxide are dissolved in 64 ml of water under an argon atmosphere. 170 ml of toluene, 10.3 g (31.8 mmol) of tetrabutylammonium bromide and 50 g (318 mmol) of 4-hydroxy-2,2,6,6-tetramethylpiperidine are added. 58.8 g (636 mmol) of epichlorohydrin are added dropwise at 45° C. The mixture is then stirred at 50° C. for 4 hours. The reaction mixture is cooled to room temperature and then poured into 1 l of ice-water, the organic phase is separated off and dried over sodium sulfate, and the residue is concentrated on a rotatory evaporator. The residue is distilled at 8·10-3 torr. Boiling point: 48° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe organic phase is separated off
  3. dry with materialdried over sodium sulfate
  4. concentrationthe residue is concentrated on a rotatory evaporator
  5. distillationThe residue is distilled at 8·10-3 torr

Sources & evidence

ORD record
ord-b5fc590e57364658bf7088356a24b7a5
Source dataset
uspto-grants-1999_11
Patent number
US05986101

Reaction notes

Loading…