Ethanol → HCID 20449614, compound

HRID 358230Notes

Reaction equation

HRID 358230 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:12]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=2)([CH3:20])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].OC1[CH2:38][C:37](C)([CH3:39])[NH:36][C:35]([CH3:42])([CH3:41])[CH2:34]1.C([Sn](=O)CCCC)CCC.C(O)C>C1(C)C(C)=CC=CC=1>[C:28]([C:23]1[CH:22]=[C:21]([C:12]([C:7]2[CH:8]=[CH:9][C:10]([OH:11])=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=2)([CH3:20])[CH2:13][CH2:14][C:15]([O:17][CH:18]2[CH2:34][C:35]([CH3:42])([CH3:41])[NH:36][C:37]([CH3:39])([CH3:38])[CH2:19]2)=[O:16])[CH:26]=[CH:25][C:24]=1[OH:27])([CH3:30])([CH3:29])[CH3:31]

Participants

6

Reactant 4

HCID 702EthanolHCID 61221Dibutyltin oxideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidineHCID 20449612HCID 20449612, compound

Product 1

HCID 20449614HCID 20449614, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

8.5 g (0.02 mol) of ethyl 4,4-bis-(3-tert.-butyl-4-hydroxyphenyl)-valerate and 3.1 g (0.02 mol) of 4-hydroxy-2,2,6,6-tetramethylpiperidine are dissolved in 200 ml of xylene. 0.1 g of dibutyltin oxide is added, and the mixture is heated at the boil under nitrogen for about 6 hours, during which the resulting ethanol is distilled off continuously. When no more ethanol distils off, the reaction solution is cooled down to room temperature, is admixed with 200 ml of water and is efficiently mixed. The organic phase is separated off, is dried over magnesium sulfate and is evaporated. The resulting oil is purified by column chromatography to give 2,2,6,6-tetramethylpiperidin-4-yl 4,4-bis-(3-tert.-butyl-4-hydroxyphenyl)-valerate in the form of a colourless solid having a melting point of 100°.

Workup

  1. distillationis distilled off continuously
  2. customWhen no more ethanol distils off
  3. additionis efficiently mixed
  4. customThe organic phase is separated off
  5. dry with materialis dried over magnesium sulfate
  6. customis evaporated
  7. customThe resulting oil is purified by column chromatography

Sources & evidence

ORD record
ord-887700689d1646858549799079a036a0
Source dataset
uspto-grants-1984_08
Patent number
US04465765

Reaction notes

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