Methanol → HCID 70627963, compound

HRID 866734Notes

Reaction equation

HRID 866734 reaction equation
[OH-].[K+].CO.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].[C:16]([N:20]=[N:21][C:22](Cl)([CH3:32])[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26])([CH3:19])([CH3:18])[CH3:17]>O.CCCCC>[C:16]([N:20]=[N:21][C:22]([S:15][C:12]1[CH:11]=[CH:10][C:9]([C:5]([CH3:8])([CH3:6])[CH3:7])=[CH:14][CH:13]=1)([CH3:32])[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:26])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 754544-Tert-ButylbenzenethiolHCID 2031823458496-97-2

Product 1

HCID 70627963HCID 70627963, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8003PentaneSolvent

Procedure

To a stirred solution of 36.2 grams (0.55 moles) of 85% potassium hydroxide in 200 ml. of methanol in a 2 liter jacketed reactor was added with cooling 91.5 grams (0.55 moles) of para-t-butylthiophenol. After the addition was complete the reaction was stirred for 20 minutes. Then a solution of approximately 138.25 grams (0.5 moles) of n-butyl 4-t-butylazo-4-chlorovalerate (prepared as in step B) in 1000 ml. of pentane was added over a 20 minute period, holding the temperature at 10°-20° C by circulating cold water through the reactor jacket. After the addition was complete the reaction was stirred for an hour at 15°-20° C, a 600 ml. portion of water added and the reaction stirred until the salts dissolved. The pentane layer was separated, washed with water, 5% HCl, water, dried over anhydrous Na2SO4, filtered and the pentane evaporated to leave 167 g. (83% yield) of n-butyl 4-t-butylazo-4-(p-t-butylthiophenoxy)valerate.

Workup

  1. additionwas added
  2. additionAfter the addition
  3. customat 10°-20° C
  4. additionAfter the addition
  5. stirringwas stirred for an hour at 15°-20° C
  6. stirringthe reaction stirred until the salts
  7. dissolutiondissolved
  8. customThe pentane layer was separated
  9. washwashed with water, 5% HCl, water
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. customthe pentane evaporated
  13. customto leave 167 g

Sources & evidence

ORD record
ord-361e102d2ef446b29e1ef7700a24270f
Source dataset
uspto-grants-1978_07
Patent number
US04101522

Reaction notes

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