Water → HCID 21387326, compound

HRID 1834334Notes

Reaction equation

HRID 1834334 reaction equation
[OH-].[K+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:10]([N:13]=[N:14][C:15]1(Cl)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH3:12])[CH3:11].O>CO>[CH:10]([N:13]=[N:14][C:15]1([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 14797Potassium HydroxideHCID 21387085HCID 21387085, compound

Product 1

HCID 21387326HCID 21387326, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 5.95 grams (.09 moles) of 85% potassium hydroxide in 50 mls of methanol in a 125 ml erlenmeyer flask was added 8.46 grams (.09 moles) of phenol and the solution stirred for 15 minutes. The solution was cooled to 20° C and 15.0 grams (.08 moles) of 1-isopropylazo-1-chlorocyclohexane (from Example 3-2) was added dropwise over 5 minutes and the reaction mixture stirred an additional hour at 20°-25° C. The reaction mixture was poured into 300 mls water and the product extracted with 200 mls of pentane. The pentane solution was separated and washed successively with 100 ml portions of 10% sodium hydroxide, water, 10% HCl (twice), 15% HCl, water, 15% sodium bisulfite solution and saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure on a rotating evaporator. The product was a yellow liquid and it weighed 15.7 grams (76.5% crude yield). The infrared spectrum of the product was in agreement with the structure of 1-isopropylazo-1-phenoxycyclohexane. Gas chromatography indicated there was also a small amount of 1-isopropylazo-1-methoxycyclohexane from a competing reaction of the methanol with the 1-isopropylazo-1-chlorocyclohexane.

Workup

  1. stirringthe reaction mixture stirred an additional hour at 20°-25° C
  2. extractionthe product extracted with 200 mls of pentane
  3. customThe pentane solution was separated
  4. washwashed successively with 100 ml portions of 10% sodium hydroxide, water, 10% HCl (twice), 15% HCl, water, 15% sodium bisulfite solution and saturated sodium bicarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe pentane evaporated under reduced pressure on a rotating evaporator
  8. customfrom a competing reaction of the methanol with the 1-isopropylazo-1-chlorocyclohexane

Sources & evidence

ORD record
ord-dabda4840565407a93468e420247f8ba
Source dataset
uspto-grants-1978_01
Patent number
US04069377

Reaction notes

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