Methanol → HCID 86735701, compound

HRID 371968Notes

Reaction equation

HRID 371968 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)([CH2:24][C:25]([CH3:33])([O:27][O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:26])[CH3:23])([CH3:19])([CH3:18])[CH3:17]>O>[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)([CH2:24][C:25]([CH3:26])([O:27][O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:33])[CH3:23])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 754544-Tert-ButylbenzenethiolHCID 20352146HCID 20352146, compound

Product 1

HCID 86735701HCID 86735701, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 1.38 g (0.021 moles) of 85% potassium hydroxide in 25 ml. of methanol in a 125 ml. erlenmeyer flask was added dropwise 3.66 grams (0.022 moles) of p-t-butylthiophenol. The reaction was stirred an additional 30 minutes and then 6.0 grams (0.0205 moles) of 2-(t-butylazo)-2-chloro-4-methyl-4-(t-butylperoxy)pentane from Example 23 was added dropwise over 30 minutes, holding the reaction temperature at 15° C with a cold water bath. The reaction was stirred an additional hour at room temperature and poured into 100 ml. of water. The product was extracted with 50 ml. of pentane, the pentane solution washed with water, dried over anhydrous sodium sulfate, filtered and the pentane evaporated on a flash evaporator. The residue weighed 8.65 g (72% yield) and its infrared spectrum was in agreement with that of the desired product.

Workup

  1. customat 15° C
  2. stirringThe reaction was stirred an additional hour at room temperature
  3. additionpoured into 100 ml
  4. extractionThe product was extracted with 50 ml
  5. washof pentane, the pentane solution washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe pentane evaporated on a flash evaporator

Sources & evidence

ORD record
ord-595aa9ed1b4b4deda814087607638367
Source dataset
uspto-grants-1978_05
Patent number
US04088642

Reaction notes

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