Hydrochloric Acid → HCID 178444357, compound

HRID 2254977Notes

Reaction equation

HRID 2254977 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][CH2:15][C@H:14](/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH3:21])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=O)C.Cl>[OH-].[K+].CO>[CH:17](/[C@H:14]1[CH2:13][CH2:12][C@H:11]([C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)[CH2:16][CH2:15]1)=[CH:18]\[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178444362HCID 178444362, compound

Product 1

HCID 178444357HCID 178444357, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

385 mg of p-[trans-4-(1E-pentenyl)cyclohexyl]phenyl acetate were dissolved in 100 ml of a 1N solution of potassium hydroxide in methanol while gassing with argon and the mixture was stirred at room temperature for 30 minutes. Subsequently, the reaction mixture was poured into 80 ml of 1N hydrochloric acid and extracted three times with 60 ml of diethyl ether each time. The organic phases were washed twice with 60 ml of water each time, dried over magnesium sulphate and concentrated. There were obtained 328 mg (100%) of p-[trans-4-(1E-pentenyl)cyclohexyl]phenol as colourless crystals; Rf-value (ethyl acetate/petroleum ether vol. 10:90) 0.17.

Workup

  1. extractionextracted three times with 60 ml of diethyl ether each time
  2. washThe organic phases were washed twice with 60 ml of water each time
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e6d85dbb9e05465b9d680af11a9688af
Source dataset
uspto-grants-1993_08
Patent number
US05238602

Reaction notes

Loading…