Ethanol → 11-Mercaptoundecanoic Acid

HRID 2380070Notes

Reaction equation

HRID 2380070 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].NC(N)=[S:17].C(O)C.[OH-].[Na+]>O>[SH:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 1781211-Bromoundecanoic acid2×HCID 2723790Thiourea

Product 1

HCID 54350211-Mercaptoundecanoic AcidYield 45.46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 200 g of 11-bromoundecanoic acid, 60 g of thiourea and 600 mL of absolute ethanol was stirred and heated at reflux for two hours. After heating was stopped a solution of 80 g of sodium hydroxide in 250 mL of water was then added dropwise. The mixture was held overnight and then heated at reflux for three hours. After cooling to room temperature a solid precipitated from solution. The reaction mixture was poured into a mixture of ice and 200 g of concentrated hydrochloric acid. The solids were filtered from solution then slurried with ice water, isolated by filtration and washed twice. The off-white solid was stored in a crystallizing dish for one week, then dried under vacuum (~1 mm of Hg) at about 45° C. The product was distilled under vacuum (~1 mm of Hg at ~160° C). NMR analysis indicated the desired product was obtained. The distilled product weighed 74.7 g representing 45.46% yield based upon the weight of starting 11-bromoundecanoic acid.

Workup

  1. temperatureheated
  2. temperatureat reflux for two hours
  3. temperatureAfter heating
  4. additionwas then added dropwise
  5. temperatureheated
  6. temperatureat reflux for three hours
  7. customprecipitated from solution
  8. additionThe reaction mixture was poured into a mixture of ice and 200 g of concentrated hydrochloric acid
  9. filtrationThe solids were filtered from solution
  10. customisolated by filtration
  11. washwashed twice
  12. waitThe off-white solid was stored in a crystallizing dish for one week
  13. customdried under vacuum (~1 mm of Hg) at about 45° C
  14. distillationThe product was distilled under vacuum (~1 mm of Hg at ~160° C)
  15. customwas obtained

Sources & evidence

ORD record
ord-fb250e77888447e2b835a6a07e4a5fc7
Source dataset
uspto-grants-1994_11
Patent number
US05364959

Reaction notes

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