Water → HCID 11335005, compound

HRID 1635777Notes

Reaction equation

HRID 1635777 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][CH3:23].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][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 1133Thioglycolic AcidHCID 10922179HCID 10922179, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 11335005HCID 11335005, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

2.02 ml of a 30% solution of sodium methoxide in methanol were added dropwise to a solution of 372 μl of thioglycolic acid in 5 ml of methanol, under an inert atmosphere. The mixture was maintained under stirring for 30 min and then a solution of 1.2 g of 1-chloro-2,5-tetradecadiyne in 6 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-heptadecadiynoic acid was recrystallized from heptane and then from hexane and finally from diisopropyl ether. The acid was thus isolated in the form of beige crystals with a yield of 49.4%.

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-heptadecadiynoic acid was recrystallized from heptane
  13. customThe acid was thus isolated in the form of beige crystals with a yield of 49.4%

Sources & evidence

ORD record
ord-8e589e3207fc47b793b9fd1ec67c5ef7
Source dataset
uspto-grants-2003_01
Patent number
US06511670B1

Reaction notes

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