Water → HCID 18673377, compound

HRID 1635780Notes

Reaction equation

HRID 1635780 reaction equation
C[O-].[Na+].[C:4]([OH:8])(=[O:7])[CH2:5][SH:6].Cl[CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].O>CO>[C:4]([OH:8])(=[O:7])[CH2:5][S:6][CH2:10][C:11]#[C:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1133Thioglycolic AcidHCID 10942334Sodium MethoxideHCID 18673378HCID 18673378, compound

Product 1

HCID 18673377HCID 18673377, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

3.2 ml of a 300% solution of sodium methoxide in methanol were added dropwise to a solution of 611 μl of thioglycolic acid in 7 ml of methanol, under an inert atmosphere. The mixture was maintained under stirring for 30 min and then a solution of 2 g of 1-chloro-2,5-pentadecadiyne in 20 ml of methanol was added under an inert atmosphere. The mixture was maintained under stirring for 20 hours at room temperature and then the reaction medium was poured over 100 ml of acid water (98 ml of water+2 ml concentrated H2SO4) and then extracted 3 times with ethyl ether. The combined organic phases were washed 3 times with water and then with a saturated aqueous solution of NaCl before being dried (Na2SO4), filtered and concentrated under vacuum in a rotary evaporator. The oily residue obtained crystallized on cooling. 3-Thia-5,8-octadecadiynoic acid was recrystallized from diisopropyl ether and thus isolated in the form of a white solid with a yield of 26%.

Workup

  1. temperatureThe mixture was maintained
  2. temperatureThe mixture was maintained
  3. stirringunder stirring for 20 hours at room temperature
  4. extractionextracted 3 times with ethyl ether
  5. washThe combined organic phases were washed 3 times with water
  6. dry with materialwith a saturated aqueous solution of NaCl before being dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum in a rotary evaporator
  9. customThe oily residue obtained
  10. customcrystallized
  11. temperatureon cooling
  12. custom3-Thia-5,8-octadecadiynoic acid was recrystallized from diisopropyl ether
  13. customthus isolated in the form of a white solid with a yield of 26%

Sources & evidence

ORD record
ord-e6681acd683a49ca93e084b7e7646b29
Source dataset
uspto-grants-2003_01
Patent number
US06511670B1

Reaction notes

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