1-Octanol → HCID 86604705, compound

HRID 1640347Notes

Reaction equation

HRID 1640347 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[CH2:10](O)[CH2:11][CH2:12]CCCCC>S(=O)(=O)(O)O.O.C1(C)C=CC=CC=1>[C:7]([OH:9])(=[O:8])[CH2:2][CH2:3][CH2:5][CH2:6][CH2:10][CH2:11][CH3:12].[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4]

Participants

6

Reactant 2

HCID 9571-OctanolHCID 6306L-Isoleucine

Product 1

HCID 86604705HCID 86604705, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolventHCID 1140TolueneSolvent

Procedure

13.1 g of isoleucine was dissolved in a solution of 10 g of concentrated sulfuric acid, 20 mL water, 20 mL of octanol, and 200 mL of toluene in a 500 mL round bottom flask equipped with a condenser and a Dean-Stark apparatus placed in an oil bath. The resulting solution was heated at reflux temperature until no more water could be distilled. The resulting solution was then cooled to room temperature, diluted with 120 mL of ethyl acetate and the organic layer washed with saturated aqueous sodium bicarbonate to neutralize acidic impurities, washed with saturated Brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the resulting liquid distilled to provide isoleucine octanoate as a colorless liquid.

Workup

  1. customequipped with a condenser
  2. customa Dean-Stark apparatus placed in an oil bath
  3. temperatureThe resulting solution was heated
  4. distillationcould be distilled
  5. additiondiluted with 120 mL of ethyl acetate
  6. washthe organic layer washed with saturated aqueous sodium bicarbonate
  7. washwashed with saturated Brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. distillationthe resulting liquid distilled

Sources & evidence

ORD record
ord-46ed4a48eb934dc8b2314a1cdd177514
Source dataset
uspto-grants-2012_02
Patent number
US08114440B2

Reaction notes

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