Hydrochloric Acid → HCID 58381686, compound

HRID 410048Notes

Reaction equation

HRID 410048 reaction equation
[CH2:1]([S:16][CH:17]([CH2:23][CH3:24])[C:18]([O:20]CC)=[O:19])[CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15].[Li+].[OH-].Cl>C(O)C.O>[CH2:1]([S:16][CH:17]([CH2:23][CH3:24])[C:18]([OH:20])=[O:19])[CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58381705HCID 58381705, compound

Product 1

HCID 58381686HCID 58381686, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
70 °C

Procedure

Ethyl 2-((3Z,6Z,9Z,12Z)-pentadeca-3,6,9,12-tetraenylthio)butanoate (14.1 g, 40.2 mmol) was dissolved in ethanol (200 mL) and added a solution of LiOH×H2O (13.5 g, 322 mmol) in water (50 mL). The resulting turbid solution was stirred at 70° C. under inert atmosphere for 90 minutes, cooled, added water (100 mL) and 3M HCl until pH=2. The mixture was extracted three times with heptane (100 mL each). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to afford 11.8 g (91% yield) of the title compound as oil.

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted three times with heptane (100 mL each)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c6bdf49e150648b59099033903541f96
Source dataset
uspto-grants-2014_06
Patent number
US08759558B2

Reaction notes

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