Pyridine → Cyclohexyl 2-(p-prenylphenyl)propionate

HRID 904924Notes

Reaction equation

HRID 904924 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:16])[C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1)[CH:2]=[C:3]([CH3:5])[CH3:4].S(Cl)(Cl)=O.N1C=CC=CC=1.[CH:27]1(O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C1C=CC=CC=1>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH3:16])[C:13]([O:15][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[O:14])=[CH:10][CH:11]=1)[CH:2]=[C:3]([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 7966CyclohexanolHCID 24386Thionyl ChlorideHCID 1754602-(4-(3-Methyl-2-butenyl)phenyl)propionic acid

Product 1

HCID 13118086Cyclohexyl 2-(p-prenylphenyl)propionateYield 65.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To an ice-cooled solution of 26.0 g of 2-(p-prenylphenyl)propionic acid in 200 ml of benzene were added dropwise 15.7 g of thionyl chloride and 10.4 g of pyridine at the same time with stirring over one hour, and then the mixture was stirred at room temperature for 30 minutes. After ice-cooling, to this mixture were added 13.0 g of cyclohexanol and 10.4 g of pyridine. The resulting mixture was stirred for 2 hours at room temperature, and then washed with 1 N hydrochloric acid, water, 5% aqueous sodium hydroxide and water successively, and dried over anhydrous mangesium sulfate. The solvent was evaporated to give 23.5 g of cyclohexyl 2-(p-prenylphenyl)propionate. b.p. 142° C./0.06 mmHg, IR νmaxneat ; 1730 cm-1.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. temperatureAfter ice-cooling, to this mixture
  3. stirringThe resulting mixture was stirred for 2 hours at room temperature
  4. washwashed with 1 N hydrochloric acid, water, 5% aqueous sodium hydroxide and water successively
  5. dry with materialdried over anhydrous mangesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-403a62d49a7a4acf8ae64b84e575bcd9
Source dataset
uspto-grants-1983_12
Patent number
US04420631

Reaction notes

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