Potassium Hydroxide → HCID 178443904, compound

HRID 622277Notes

Reaction equation

HRID 622277 reaction equation
[CH2:1]([C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19]C(=O)OCCC)=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[OH-].[K+]>C(O)COCCO.O>[CH2:1]([C@H:7]1[CH2:8][CH2:9][C@H:10]([C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[CH2:11][CH2:12]1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178443905HCID 178443905, compound

Product 1

HCID 178443904HCID 178443904, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 22315797HCID 22315797, compoundSolvent

Procedure

A mixture of 3.33 g of crude propyl p-[trans-4-(5-hexenyl)cyclohexyl]phenylcarbamate and 150 ml of a 10 percent solution of potassium hydroxide in diethylene glycol/water (vol. 4:1) was boiled at 120° C. for 2 hours, then cooled to room temperature and partitioned between 150 ml of methylene chloride and 150 ml of water. The aqueous phase was back-extracted twice with 150 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the brown, crystalline residue (3 g) on 70 g of silica gel with ethyl acetate/petroleum ether (vol. 20:80) gave 2.18 g (88%) of p-[trans-4-(5-hexenyl)cyclohexyl]aniline as light yellowish crystals (purity 98.1%); Rf value 0.20 (ethyl acetate/petroleum ether vol. 1:5).

Workup

  1. customfor 2 hours
  2. custompartitioned between 150 ml of methylene chloride and 150 ml of water
  3. extractionThe aqueous phase was back-extracted twice with 150 ml of methylene chloride each time
  4. washThe organic phases were washed twice with 100 ml of water each time
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bb1c1ce90624f7eb3c73b014a7dc163
Source dataset
uspto-grants-1988_09
Patent number
US04770503

Reaction notes

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