Water → HCID 18673380, compound

HRID 1635782Notes

Reaction equation

HRID 1635782 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][CH3:21].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][CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1133Thioglycolic AcidHCID 10942334Sodium MethoxideHCID 18673386HCID 18673386, compound

Product 1

HCID 18673380HCID 18673380, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

3.85 ml of a 30% solution of sodium methoxide in methanol were added dropwise to a solution of 742 μl of thioglycolic acid in 8 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-dodecadiyne in 20 ml of methanol was added under an inert atmosphere. The mixture was maintained under stirring for 15 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 at cold temperature. 3-Thia-5,8-pentadecadiynoic acid was recrystallized from diisopropyl ether.

Workup

  1. temperatureThe mixture was maintained
  2. temperatureThe mixture was maintained
  3. stirringunder stirring for 15 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 at cold temperature
  11. custom3-Thia-5,8-pentadecadiynoic acid was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-a4e1a1963f764fe3a73082a212fe65c1
Source dataset
uspto-grants-2003_01
Patent number
US06511670B1

Reaction notes

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