Ethanol → HCID 20449618, compound

HRID 2049189Notes

Reaction equation

HRID 2049189 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=2)([CH3:16])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C:3]=1[C:28]([CH3:31])([CH3:30])[CH3:29].[CH3:32][N:33]1[C:38](C)([CH3:39])[CH2:37]C(O)[CH2:35][C:34]1([CH3:43])[CH3:42].[NH2-].[Li+].C(O)C>C1(C)C=C(C)C=C(C)C=1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:18]=2)([CH3:16])[CH2:9][CH2:10][C:11]([O:13][CH:14]2[CH2:35][C:34]([CH3:43])([CH3:42])[N:33]([CH3:32])[C:38]([CH3:39])([CH3:37])[CH2:15]2)=[O:12])=[CH:4][C:3]=1[C:28]([CH3:30])([CH3:29])[CH3:31]

Participants

6

Reactant 4

HCID 702EthanolHCID 24532Lithium amideHCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-HCID 20449612HCID 20449612, compound

Product 1

HCID 20449618HCID 20449618, compound

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Conditions

Temperature
160 °C

Procedure

42.7 g of ethyl 4,4-di-(4-hydroxy-3-t-butyl-phenyl)-valerate and 17.1 g of 1,2,2,6,6-pentamethyl-4-hydroxy-piperidine in 120 ml of mesitylene, with the addition of 100 mg of lithium amide as the catalyst, are heated to 160° C. in a nitrogen atmosphere for 5 hours, whilst stirring. During this time, the ethanol formed distils off in the stream of nitrogen and can be measured in a cold trap. After cooling, 100 ml of toluene are added to the batch and the solution is washed with water, dried with calcium chloride and evaporated in vacuo. The crystalline residue is recrystallised from acetonitrile or chlorobenzene. In this way 1,2,2,6,6-pentamethyl-piperidin-4-yl 4,4-di-(4-hydroxy-3-t-butyl-phenyl)-valerate (stabiliser no. 2) is obtained as a white crystalline powder with a melting point of 203° C.

Workup

  1. customdistils off in the stream of nitrogen
  2. customcan be measured in a cold trap
  3. temperatureAfter cooling
  4. addition100 ml of toluene are added to the batch
  5. washthe solution is washed with water
  6. dry with materialdried with calcium chloride
  7. customevaporated in vacuo
  8. customThe crystalline residue is recrystallised from acetonitrile or chlorobenzene

Sources & evidence

ORD record
ord-46843a188d0845a9b348e7c2e0fd695d
Source dataset
uspto-grants-1980_04
Patent number
US04197236

Reaction notes

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