Epichlorohydrin → 4-(2,3-Epoxypropoxy)-1-octyloxy-2,2,6,6-tetramethylpiperidine

HRID 52390Notes

Reaction equation

[OH-].[Na+].[CH2:3]([O:11][N:12]1[C:17]([CH3:19])([CH3:18])[CH2:16][CH:15]([OH:20])[CH2:14][C:13]1([CH3:22])[CH3:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:23]([CH:25]1[O:27][CH2:26]1)Cl.C(=O)(O)[O-].[Na+]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([O:11][N:12]1[C:17]([CH3:19])([CH3:18])[CH2:16][CH:15]([O:20][CH2:23][CH:25]2[O:27][CH2:26]2)[CH2:14][C:13]1([CH3:21])[CH3:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

Conditions

Temperature: 30 °C

Procedure

100 g (2.5 mol) of sodium hydroxide are dissolved in 100 ml of water in a 750 ml sulfonation flask fitted with mechanical stirrer, thermometer, dropping funnel and condenser. 71.9 g (0.25 mol) of 1-octyloxy-2,2,6,6-tetramethyl-4-hydroxypiperidine and 16.1 g (0.05 mol) of tetrabutylammonium bromide are added at 20° C. The mixture is warmed to 30° C. with vigorous stirring. A solution of 277.5 g (3 mol) of epichlorohydrin and 71.9 g (0.25 mol) of 1-octyloxy-2,2,6,6-tetramethyl-4-hydroxypiperidine is then added dropwise at 35° C. over the course of 75 minutes. The reaction solution is stirred at room temperature for 16 hours and poured onto 1 kg of ice and 100 g of sodium bicarbonate. The organic phase is separated off. The water phase is extracted with ethyl acetate. The two organic phases are washed with sodium chloride-saturated water, dried over sodium sulfate and evaporated on a Rotavap.

Workup

customfitted with mechanical stirrer
customThe organic phase is separated off
extractionThe water phase is extracted with ethyl acetate
washThe two organic phases are washed with sodium chloride-saturated water
dry with materialdried over sodium sulfate
customevaporated on a Rotavap

Sources & evidence

ORD record: ord-cb646b4ed9e74716b41f57c77ae11bab
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616637

Reaction notes

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