Toluene → HCID 19438288, compound

HRID 1734735Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.[OH-:12].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[C:27]1([CH3:33])C=CC=C[CH:28]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[O:12]1[CH2:28][CH:27]1[CH2:33][N:5]1[C:4]([CH3:11])([CH3:10])[CH2:3][CH:2]([O:1][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:7][C:6]1([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 65 °C

Procedure

201 g (1.28 mol) of 4-hydroxy-2,2,6,6-tetramethylpiperidine, 21.7 g (64 mmol) of tetrabutylammonium hydrogensulfate, 1.3 l of toluene and 256 g of sodium hydroxide (dissolved in 256 g of water) are introduced into a 2.5 l sulfonation flask fitted with glass stirrer, thermometer, dropping funnel and condenser. The mixture is warmed to 65° C., and 350 g (1.4 mol) of 1-bromododecane are added dropwise over the course of 1.5 hours. The mixture is then stirred for 15 hours under reflux, cooled to room temperature and poured onto ice, the organic phase is washed with water and dried over sodium sulfate, and the solvent is removed on a rotary evaporator. The residue is distilled at 8.10-3 mmHg over a Vigreux column, giving 150 g (36%) of a clear liquid having the boiling point 124°-126° C.

Workup

customfitted with glass stirrer
temperatureunder reflux
temperaturecooled to room temperature
additionpoured onto ice
washthe organic phase is washed with water
dry with materialdried over sodium sulfate
customthe solvent is removed on a rotary evaporator
distillationThe residue is distilled at 8.10-3 mmHg over a Vigreux column

Sources & evidence

ORD record: ord-7bb716d9cbe14d939142df95dd0c4eff
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05534618

Reaction notes

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