trans-2-Decenoic acid → HCID 25231028, compound

HRID 1042373Notes

Reaction equation

HRID 1042373 reaction equation
[C:1]([OH:12])(=[O:11])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>S(Cl)(Cl)=O.O>[CH2:1]([O:11][C:1](=[O:12])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 5282724trans-2-Decenoic acid

Product 1

HCID 25231028HCID 25231028, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Trans-2-decenoic acid was dissolved in thionyl chloride (10 ml) and treated in water bath for 3 hours to distill off excess thionyl chloride. Trans-2-decen-1-ol (30 ml) was added to chloride of trans-2-decenoic acid and refluxed in water bath for 2 hours. After cooling, the reaction mixture was added to 1N HCl (80 ml) to be acidic and distributed with EtOAc. The distributed liquid was purified with column chromatography (developing solvent: C6H14-EtOAc (3:1)) after concentration, and trans-2-decenoic acid-trans-2-decenyl ester shown in the following was isolated.

Workup

  1. distillationto distill off excess thionyl chloride
  2. additionTrans-2-decen-1-ol (30 ml) was added to chloride of trans-2-decenoic acid
  3. temperaturerefluxed in water bath for 2 hours
  4. temperatureAfter cooling
  5. additionthe reaction mixture was added to 1N HCl (80 ml)
  6. customThe distributed liquid was purified with column chromatography (developing solvent: C6H14-EtOAc (3:1))
  7. concentrationafter concentration, and trans-2-decenoic acid-trans-2-decenyl ester
  8. customfollowing was isolated

Sources & evidence

ORD record
ord-2d3100e163f445568b4ca5def9b3278d
Source dataset
uspto-grants-2013_10
Patent number
US08557864B2

Reaction notes

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