Potassium Hydroxide → HCID 178444345, compound

HRID 2073133Notes

Reaction equation

HRID 2073133 reaction equation
[CH:1](/[C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)OCCC)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[CH:2]\[CH2:3][CH2:4][CH3:5].[OH-].[K+]>C(O)COCCO.O>[CH:1](/[C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1)=[CH:2]\[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178444346HCID 178444346, compound

Product 1

HCID 178444345HCID 178444345, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 22315797HCID 22315797, compoundSolvent

Procedure

A mixture of 118 mg of propyl p-[trans-4-(trans-1-pentenyl)cyclohexyl]phenylcarbamate and 12.5 ml of a 10% solution of potassium hydroxide in diethylene glycol/water (vol. 4:1) was boiled at 120° C. for 1 hour, then cooled to room temperature and partitioned between 70 ml of diethyl ether and 70 ml of water. The aqueous phase was back-extracted twice with 70 ml of diethyl ether each time. The organic phases were washed twice with 50 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the brown, crystalline residue (150 mg) on 35 g of silica gel with ethyl acetate/petroleum ether (vol. 15:85) gave 76.6 mg (88%) of p-[trans-4-(trans-1-pentenyl)cyclohexyl]aniline as slightly yellowish crystals; purity 97%; Rf-value 0.24 (ethyl acetate/petroleum ether, vol. 1:5).

Workup

  1. customfor 1 hour
  2. custompartitioned between 70 ml of diethyl ether and 70 ml of water
  3. extractionThe aqueous phase was back-extracted twice with 70 ml of diethyl ether each time
  4. washThe organic phases were washed twice with 50 ml of water each time
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8e12e3156a214024802afabbc3294528
Source dataset
uspto-grants-1990_04
Patent number
US04915480

Reaction notes

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