Phenol → 4-t-Butylazo-4-phenoxypentyl alcohol

HRID 866740Notes

Reaction equation

HRID 866740 reaction equation
[OH-].[K+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O:13][CH2:14][CH2:15][CH2:16][C:17]([N:20]=[N:21][C:22]([CH3:25])([CH3:24])[CH3:23])(Cl)[CH3:18])(=O)C>CO>[C:22]([N:21]=[N:20][C:17]([O:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([CH3:18])[CH2:16][CH2:15][CH2:14][OH:13])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 233459014-t-Butylazo-4-chloropentyl acetate

Product 1

HCID 706285794-t-Butylazo-4-phenoxypentyl alcoholYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of 1.72 grams (0.026 moles) of 85% KOH in 20 mls. of methanol in a 100 ml. 3-necked round bottom flask equipped with a magnetic stirrer and thermometer was added 2.44 grams (0.026 moles) of phenol. The reaction was stirred for 15 minutes at 15° C and then 6.25 grams (0.025 moles) of the chloro compound prepared in step B was added dropwise over 20 minutes. The reaction was stirred an additional 30 minutes at room temperature. A sample was withdrawn and checked by infrared analysis which indicated the acetate was partially saponified to the alcohol. An additional 1.5 grams of KOH was added to the reaction mixture and the reaction stirred another 15 minutes. Infrared analysis indicated the saponification was complete so the reaction mixture was diluted with 200 mls. water and extracted with pentane. The pentane solution was washed with saturated NaHCO3 solution, dried over anhydrous sodium sulfate, filtered and the pentane evaporated to leave 5.2 grams (80% yield) of the desired alcohol.

Workup

  1. custom3-necked round bottom flask equipped with a magnetic stirrer
  2. stirringThe reaction was stirred an additional 30 minutes at room temperature
  3. customA sample was withdrawn
  4. additionAn additional 1.5 grams of KOH was added to the reaction mixture
  5. stirringthe reaction stirred another 15 minutes
  6. additionwas diluted with 200 mls
  7. extractionwater and extracted with pentane
  8. washThe pentane solution was washed with saturated NaHCO3 solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe pentane evaporated

Sources & evidence

ORD record
ord-50b9e01051b74e76aabd145990da1b75
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

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