Octanoyl chloride → HCID 21421692, compound

HRID 259417Notes

Reaction equation

HRID 259417 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[CH:5]=[C:6]([CH3:9])[C:7]=1[OH:8].[C:20](Cl)(=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>[Na].C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[CH:5]=[C:6]([CH3:9])[C:7]=1[O:8][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 2

HCID 8124Octanoyl chlorideHCID 20494021HCID 20494021, compound

Product 1

HCID 21421692HCID 21421692, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 5360545SodiumSolvent

Procedure

20 Parts of 4-(3',5'-dimethyl-4'-hydroxyphenyl)-2,2,6,6-tetramethylpiperidine were dissolved in 1000 parts of sodium dried xylene and heated to reflux whilst stirred. 6.3 Parts of octanoyl chloride dissolved in a small amount of xylene were added to the refluxing solution dropwise. The solution was heated at reflux overnight, allowed to cool and filtered. The filtrate was evaporated to low bulk, dissolved in ether and washed with 2% aqueous sodium hydroxide and water. The organic phase was dried over magnesium sulphate and evaporated under reduced pressure. The residue was distilled under reduced pressure to yield 10.3 parts of the desired product having boiling point 175°-178°/0.05 mm and the following elemental analysis

Workup

  1. temperatureheated
  2. temperatureto reflux whilst
  3. additionwere added to the refluxing solution dropwise
  4. temperatureThe solution was heated
  5. temperatureat reflux overnight
  6. temperatureto cool
  7. filtrationfiltered
  8. customThe filtrate was evaporated to low bulk
  9. dissolutiondissolved in ether
  10. washwashed with 2% aqueous sodium hydroxide and water
  11. dry with materialThe organic phase was dried over magnesium sulphate
  12. customevaporated under reduced pressure
  13. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-66fb720299134ed19769cdf7c6077941
Source dataset
uspto-grants-1977_07
Patent number
US04038280

Reaction notes

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