Butyl bromide → HCID 21421686, compound

HRID 259418Notes

Reaction equation

HRID 259418 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]([CH3:17])([CH3:16])[CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:20](Br)[CH2:21][CH2:22][CH3:23]>C(O)C>[CH2:20]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][C:10]([CH3:17])([CH3:16])[NH:11][C:12]([CH3:15])([CH3:14])[CH2:13]2)=[CH:4][CH:3]=1)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 14798Sodium HydroxideHCID 21421695HCID 21421695, compound

Product 1

HCID 21421686HCID 21421686, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

1 Part of 4-(4-hydroxyphenyl)-2,2,6,6-tetramethylpiperidine was dissolved in warm ethanol and treated with 0.172 parts of sodium hydroxide dissolved in ethanol. The solution was stirred and heated to reflux whilst 0.65 parts of n-butyl bromide dissolved in ethanol was added. The solution was heated at reflux overnight and then evaporated under reduced pressure. The residue was dissolved in ether and washed with water, sodium hydroxide solution (3%) and further water. The organic layer was dried (MgSO4) and evaporated under reduced pressure. The residue was distilled to yield the desired product having b.p. 160°/0.2 mm. and the following elemental analysis:

Workup

  1. temperatureheated
  2. additionwas added
  3. temperatureThe solution was heated
  4. temperatureat reflux overnight
  5. customevaporated under reduced pressure
  6. dissolutionThe residue was dissolved in ether
  7. washwashed with water, sodium hydroxide solution (3%) and further water
  8. dry with materialThe organic layer was dried (MgSO4)
  9. customevaporated under reduced pressure
  10. distillationThe residue was distilled

Sources & evidence

ORD record
ord-e7832b0278c74de7ae5401c144b68613
Source dataset
uspto-grants-1977_07
Patent number
US04038280

Reaction notes

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