Acetic Acid → HCID 21541376, compound

HRID 1075889Notes

Reaction equation

HRID 1075889 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]([CH3:17])([CH3:16])[CH2:9]2)[CH2:4][CH2:3]1.[C:18](O)(=[O:20])[CH3:19]>C1(C)C(C)=CC=CC=1>[C:18]([O:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH:8]2[CH2:9][C:10]([CH3:17])([CH3:16])[NH:11][C:12]([CH3:15])([CH3:14])[CH2:13]2)[CH2:4][CH2:3]1)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 22288041HCID 22288041, compound

Product 1

HCID 21541376HCID 21541376, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

7 parts of 4-(4'-hydroxycyclohexyl)-2,2,6,6-tetramethylpiperidine were dissolved in xylene by warming 1.7 parts of acetic acid and 0.5 part of tetra-n-butyl-ortho-titanate were added and the solution allowed to stir and reflux for 48 hours. Water was continuously removed from the reaction. The xylene was removed under reduced pressure and the residue treated with 0.5 part carbon, 0.5 part sodium carbonate and water. The mixture was stirred and heated at reflux for 1 hour. The mixture was then filtered and the filtrate extracted with ether. The organic layer was dried over magnesium sulphate and evaporated under reduced pressure. The residue was distilled under reduced pressure to yield the desired product boiling at 114°-7°C/0.1mm and having the following elemental analysis:

Workup

  1. additionwere added
  2. temperaturereflux for 48 hours
  3. customWater was continuously removed from the reaction
  4. customThe xylene was removed under reduced pressure
  5. additionthe residue treated with 0.5 part carbon, 0.5 part sodium carbonate and water
  6. stirringThe mixture was stirred
  7. temperatureheated
  8. temperatureat reflux for 1 hour
  9. filtrationThe mixture was then filtered
  10. extractionthe filtrate extracted with ether
  11. dry with materialThe organic layer was dried over magnesium sulphate
  12. customevaporated under reduced pressure
  13. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-aae7e4f397e34467ae903057a4b801b9
Source dataset
uspto-grants-1976_05
Patent number
US03954779

Reaction notes

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