Isobutanol → Isobutyl 2-(p-prenylphenyl)propionate

HRID 904923Notes

Reaction equation

HRID 904923 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.[CH2:21](O)[CH:22]([CH3:24])[CH3:23]>N1C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([CH3:16])[C:13]([O:15][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:14])=[CH:10][CH:11]=1)[CH:2]=[C:3]([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 6560IsobutanolHCID 24386Thionyl ChlorideHCID 1754602-(4-(3-Methyl-2-butenyl)phenyl)propionic acid

Product 1

HCID 13118085Isobutyl 2-(p-prenylphenyl)propionateYield 73.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 1049PyridineSolvent

Conditions

Temperature
4 °C

Procedure

To a solution of 21.8 g of 2-(p-prenylphenyl)propionic acid in 17.6 ml of pyridine and 200 ml of benzene was added dropwise a solution of 7.9 ml of thionyl chloride in 15 ml of benzene with stirring at 4° C. After one hour, 14.8 g of isobutyl alcohol was added. The mixture was stirred at room temperature for one hour and then at 60° C. for 2 hours. After cooling, the solution was washed with water, 2 N hydrochloric acid, water, 5% aqueous sodium hydroxide and water successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 20.1 g of isobutyl 2-(p-prenylphenyl)propionate. b.p. 126°-127° C./0.10 mmHg, IR νmaxneat ; 1730 cm-1.

Workup

  1. stirringThe mixture was stirred at room temperature for one hour
  2. waitat 60° C. for 2 hours
  3. temperatureAfter cooling
  4. washthe solution was washed with water, 2 N hydrochloric acid, water, 5% aqueous sodium hydroxide and water successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e91dd45e9b644125b6e4dab94dd40d78
Source dataset
uspto-grants-1983_12
Patent number
US04420631

Reaction notes

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