O-Xylene → HCID 86737387, compound

HRID 1732726Notes

Reaction equation

HRID 1732726 reaction equation
[CH2:1]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:2]([C:12]([O:14][CH2:15][CH3:16])=[O:13])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6].[CH2:22]([N:29]1[C:34]([CH3:36])([CH3:35])CC(O)[CH2:31][C:30]1([CH3:39])[CH3:38])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:40]1([CH3:47])[C:41](C)=[CH:42][CH:43]=[CH:44][CH:45]=1.[Li]N>C(O)C>[CH2:22]([N:29]1[C:30]([CH3:38])([CH3:39])[CH2:31][CH:20]([O:19][C:17]([CH2:1][C:2]([C:12]([O:14][CH:15]2[CH2:31][C:30]([CH3:39])([CH3:38])[N:29]([CH2:47][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]([CH3:36])([CH3:35])[CH2:16]2)=[O:13])([C:7]([O:9][CH:10]2[CH2:39][C:30]([CH3:31])([CH3:38])[N:29]([CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:34]([CH3:35])([CH3:36])[CH2:11]2)=[O:8])[CH2:3][CH2:4][CH2:5][CH3:6])=[O:18])[CH2:21][C:34]1([CH3:35])[CH3:36])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 1036024-Piperidinol, 2,2,6,6-tetramethyl-1-(phenylmethyl)-HCID 122968851,2,2-Hexanetricarboxylic acid, triethyl esterHCID 178506930HCID 178506930, compound

Product 1

HCID 86737387HCID 86737387, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30.2 g (0.1 mol) of triethyl hexane-1,2,2-tricarboxylate, 74.2 g (0.3 mol) of 1-benzyl-2,2,6,6-tetramethyl-4-hydroxypiperidine and 50 ml of xylene are warmed to 130° and mixed with 0.8 g of LiNH2. The ethanol formed is distilled off continuously. The solution is kept at the above temperature for 3 hours, so that it can then be kept at 150° for a further 2 hours. After cooling, the residue is taken up in toluene, a little glacial acetic acid is added to the solution and the latter is washed with H2O. After drying over Na2SO4, the solvent is distilled off in vacuo. Tris-(1-benzyl-2,2,6,6-tetramethyl-4-piperidinyl)hexane-1,2,2-tricarboxylate is obtained as a powdery residue. (Compound No. 1).

Workup

  1. distillationis distilled off continuously
  2. waitcan then be kept at 150° for a further 2 hours
  3. temperatureAfter cooling
  4. additiona little glacial acetic acid is added to the solution
  5. washthe latter is washed with H2O
  6. dry with materialAfter drying over Na2SO4
  7. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-f49222781930484c9ba96ee7d95aca35
Source dataset
uspto-grants-1980_12
Patent number
US04238613

Reaction notes

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