Acetic Acid → Butyl-(3,5-di-tert.butyl-4-hydroxybenzyl)malonic acid-bis(2,3,6-trimethyl-2,6-diethyl-4-piperidinyl) ester

HRID 2049725Notes

Reaction equation

HRID 2049725 reaction equation
[CH3:1][C:2]1([CH2:36][CH3:37])[CH:7]([CH3:8])[CH:6]([O:9][C:10](=[O:32])[CH:11]([CH2:28][CH2:29][CH2:30][CH3:31])[C:12]([O:14][CH:15]2[CH2:20][C:19]([CH3:23])([CH2:21][CH3:22])[NH:18][C:17]([CH3:26])([CH2:24][CH3:25])[CH:16]2[CH3:27])=[O:13])[CH2:5][C:4]([CH3:35])([CH2:33][CH3:34])[NH:3]1.[C:38]([C:42]1[CH:43]=[C:44]([CH:49]=[C:50]([C:53]([CH3:56])([CH3:55])[CH3:54])[C:51]=1[OH:52])[CH2:45]N(C)C)([CH3:41])([CH3:40])[CH3:39].[NH2-].[Li+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:26][C:17]1([CH2:24][CH3:25])[CH:16]([CH3:27])[CH:15]([O:14][C:12](=[O:13])[C:11]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:45][C:44]2[CH:49]=[C:50]([C:53]([CH3:54])([CH3:56])[CH3:55])[C:51]([OH:52])=[C:42]([C:38]([CH3:40])([CH3:39])[CH3:41])[CH:43]=2)[C:10]([O:9][CH:6]2[CH2:5][C:4]([CH3:35])([CH2:33][CH3:34])[NH:3][C:2]([CH3:1])([CH2:36][CH3:37])[CH:7]2[CH3:8])=[O:32])[CH2:20][C:19]([CH3:23])([CH2:21][CH3:22])[NH:18]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24532Lithium amideHCID 66609Phenol, 4-[(dimethylamino)methyl]-2,6-bis(1,1-dimethylethyl)-HCID 20343463Butylmalonic acid-bis(2,3,6-trimethyl-2,6-diethyl-4-piperidinyl)ester

Product 1

HCID 20343468Butyl-(3,5-di-tert.butyl-4-hydroxybenzyl)malonic acid-bis(2,3,6-trimethyl-2,6-diethyl-4-piperidinyl) ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

26.2 g (0.05 mole) of butylmalonic acid-bis(2,3,6-trimethyl-2,6-diethyl-4-piperidinyl)ester and 13.2 g (0.05 mole) of N-(3,5-di-tert.butyl-4-hydroxybenzyl) dimethylamine are dissolved in 200 ml of toluene. After the addition of 0.25 g of lithium amide, the mixture is refluxed for 4 hours. After cooling, the mixture is neutralised with 1.5 ml of 1% acetic acid, and the organic phase is repeatedly washed with water. After drying over Na2SO4, the solution is concentrated in vacuo. As residue there is obtained butyl-(3,5-di-tert.butyl-4-hydroxybenzyl)malonic acid-bis(2,3,6-trimethyl-2,6-diethyl-4-piperidinyl) ester in the form of viscous oil (Compound No. 32).

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureAfter cooling
  3. washthe organic phase is repeatedly washed with water
  4. dry with materialAfter drying over Na2SO4
  5. concentrationthe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-19db1396771d4c0ea867166a1302f815
Source dataset
uspto-grants-1980_04
Patent number
US04198334

Reaction notes

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