Stearoyl chloride → Octadecanoic acid, [9-(acetyloxy)-3,8,10-triethyl-7,8,10-trimethyl-1,5-dioxa-9-azaspiro[5.5]undec-3-yl]methyl ester

HRID 900412Notes

Reaction equation

HRID 900412 reaction equation
[CH2:1]([C:3]1([CH2:21][OH:22])[CH2:8][O:7][C:6]2([CH2:13][C:12]([CH2:15][CH3:16])([CH3:14])[NH:11][C:10]([CH2:18][CH3:19])([CH3:17])[CH:9]2[CH3:20])[O:5][CH2:4]1)[CH3:2].[C:23](Cl)(=[O:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>N1C=CC=CC=1.O>[C:23]([O:22][CH2:21][C:3]1([CH2:1][CH3:2])[CH2:4][O:5][C:6]2([CH2:13][C:12]([CH2:15][CH3:16])([CH3:14])[N:11]([O:7][C:6](=[O:5])[CH3:9])[C:10]([CH2:18][CH3:19])([CH3:17])[CH:9]2[CH3:20])[O:7][CH2:8]1)(=[O:41])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

5

Reactant 2

HCID 8212Stearoyl chlorideHCID 22182240HCID 22182240, compound

Product 1

HCID 22182236Octadecanoic acid, [9-(acetyloxy)-3,8,10-triethyl-7,8,10-trimethyl-1,5-dioxa-9-azaspiro[5.5]undec-3-yl]methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

12 g (0.037 mol) of 3,8,10-triethyl-7,8,10-trimethyl-1,5-dioxa-9-azaspiro[5.5]undec-3-ylmethanol (for method of preparation, see U.S. Pat. No. 4,105,626) are dissolved in 40 ml of pyridine and admixed with 11.7 g (0.039 mol) of stearoyl chloride. After stirring for 18 hours at room temperature, the reaction mixture is diluted with 200 ml of water and extracted with 2×50 ml of methyl-t-butylether. After distilling off the solvent, the resulting stearoyl nitroxide is converted by a method analogous to Example A 30 into the compound 144 which is obtained in the form of a colourless oil.

Workup

  1. extractionextracted with 2×50 ml of methyl-t-butylether
  2. distillationAfter distilling off the solvent
  3. customis obtained in the form of a colourless oil

Sources & evidence

ORD record
ord-f8c97421349649b7bc5ff15148543495
Source dataset
uspto-grants-2008_04
Patent number
US07358365B2

Reaction notes

Loading…