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

HRID 52391

Reaction equation

HRID 52391 reaction equation
[OH-:1].[Na+].[C:3]1([CH3:9])C=CC=C[CH:4]=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>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:17][C:15]1([CH3:18])[CH2:16][CH:11]([O:10][CH2:9][CH:3]2[O:1][CH2:4]2)[CH2:12][C:13]([CH3:20])([CH3:19])[NH:14]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 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

64.0 g of sodium hydroxide (1.6 mol) are dissolved in 64 ml of water under argon in a 750 ml sulfonation flask fitted with mechanical stirrer, condenser, thermometer and 100 ml dropping funnel. 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 epichlorohyrdin 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 poured into 1 l of ice water, and the organic phase is separated off, dried using sodium sulfate and evaporated on a rotary evaporator. The residue is distilled at 8×10-3 mmHg. Boiling point: 48° C., yield: 28 g (41%). GC: 98%.

Workup

  1. customfitted with mechanical stirrer, condenser
  2. addition58.8 g (636 mmol) of epichlorohyrdin are added dropwise at 45° C
  3. temperatureThe reaction mixture is cooled to room temperature
  4. customthe organic phase is separated off
  5. customdried
  6. customevaporated on a rotary evaporator
  7. distillationThe residue is distilled at 8×10-3 mmHg

Sources & evidence

ORD record
ord-a31b47d114774dcabb8fc53bf13ce8aa
Source dataset
uspto-grants-1997_04
Patent number
US05616637

Linked notes

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