Water → 4-(Octylthio)butanoic acid

HRID 2380074Notes

Reaction equation

HRID 2380074 reaction equation
O.[CH2:2]([SH:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:11]1(=[O:16])[O:15][CH2:14][CH2:13][CH2:12]1>C(O)C>[CH2:2]([S:10][CH2:14][CH2:13][CH2:12][C:11]([OH:16])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 7302Gamma-ButyrolactoneHCID 81441-Octanethiol

Product 1

HCID 3489844-(Octylthio)butanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

An apparatus was provided including a two liter, 4-neck, round bottom flask equipped with an alcohol thermometer, an overhead mechanical stirrer, a water-cooled condenser and a nitrogen purge. Into this reactor gradually were added 23 g of sodium into 1,200 ml of absolute ethanol previously added. After all of the sodium had reacted the solution was stirred overnight under a slow nitrogen flow. 1-octanethiol, 146.28 g, was added to the mixture and an addition funnel and heating mantel were added to the reactor. In 200 ml of ethanol, 129.13 g of butyrolactone was added dropwise to the ethanol solution at reflux temperature. The resulting mixture was heated at reflux overnight. The ethanol was then removed from the reaction mixture and the residue was dissolved in water. The aqueous solution was washed with methylene chloride. The aqueous solution was then added to an ice/sulfuric acid mixture and the product extracted with methylene chloride. The methylene chloride solution was washed with water, dried with sodium sulfate, filtered and concentrated under vacuum with heating. The liquid product solidified upon cooling to room temperature. There was provided 219 g of 4-(n-octylthio)butyric acid. The solid exhibited a melting point of 33°-34.5° C.

Workup

  1. customAn apparatus was provided
  2. customa nitrogen purge
  3. additionInto this reactor gradually were added 23 g of sodium into 1,200 ml of absolute ethanol
  4. additionpreviously added
  5. customAfter all of the sodium had reacted the solution
  6. temperatureheating mantel
  7. additionwere added to the reactor
  8. temperatureat reflux temperature
  9. temperatureThe resulting mixture was heated
  10. temperatureat reflux overnight
  11. customThe ethanol was then removed from the reaction mixture
  12. dissolutionthe residue was dissolved in water
  13. washThe aqueous solution was washed with methylene chloride
  14. additionThe aqueous solution was then added to an ice/sulfuric acid mixture
  15. extractionthe product extracted with methylene chloride
  16. washThe methylene chloride solution was washed with water
  17. dry with materialdried with sodium sulfate
  18. filtrationfiltered
  19. concentrationconcentrated under vacuum
  20. temperaturewith heating

Sources & evidence

ORD record
ord-9b04b354a4a8437392234f6a99230a62
Source dataset
uspto-grants-1994_11
Patent number
US05364959

Reaction notes

Loading…