Sulfuric Acid → HCID 22186347, compound

HRID 1297330Notes

Reaction equation

HRID 1297330 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[SH:10][CH:11]([CH3:15])[C:12]([OH:14])=O.S(=O)(=O)(O)O>O.C1(C)C=CC=CC=1>[SH:10][CH:11]([CH3:15])[C:12]([O:1][CH2:2][C:3]([CH2:8][O:9][C:12](=[O:14])[CH:11]([SH:10])[CH3:15])([CH2:6][O:7][C:12](=[O:14])[CH:11]([SH:10])[CH3:15])[CH2:4][O:5][C:12](=[O:14])[CH:11]([SH:10])[CH3:15])=[O:14]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 8285PentaerythritolHCID 62326(+-)-2-Mercaptopropionic acid

Product 1

HCID 22186347HCID 22186347, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1140TolueneSolvent

Procedure

To a 500-milliliter round-bottom flask equipped with a magnetic stirring bar, a water separator, and a condenser were added 27.23 grams (0.200 mol) of pentaerythritol, 90.22 grams (0.850 mol) of 2-mercaptopropionic acid, 100 milliliters of toluene, and 0.5 milliliter of concentrated sulfuric acid. The mixture was heated under reflux with stirring. After about 2 days, the solid material had disappeared, and about 17 milliliters (0.94 mol) of water had been collected by the water separator. Upon cooling to room temperature, the mixture was extracted with 30 milliliters of saturated NaHCO3 solution and washed with two 50-milliliter portions of water. The organic layer was dried over anhydrous MgSO4, and most of the toluene and residual 2-mercaptopropionic acid were removed by distillation under vacuum. Recrystallization of the residue from ethanol gave 86.0 grams (88.4%, calcd. 97.3 grams) of pentaerythritol tetrakis(2-mercaptopropionate) as a white solid, mp 93-96° C.; 1H NMR (in CDCl3 w/TMS, ppm): 4.17-4.30 (AB m, 8H, CH2O), 3.50 (pentuplet, 4H, CHSH), 2.17 (d of d, 4H, SH), 1.51 (d, 12H, CH3); {1H}13C NMR (in CDCl3 w/TMS, ppm): 172.79 (C═O), 62.47 (CH2O), 43.05 [C(CH2)4], 35.43 (CCHSH), 20.94 (CH3).

Workup

  1. customTo a 500-milliliter round-bottom flask equipped with a magnetic stirring bar
  2. temperatureThe mixture was heated
  3. temperatureunder reflux
  4. extractionthe mixture was extracted with 30 milliliters of saturated NaHCO3 solution
  5. washwashed with two 50-milliliter portions of water
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. custommost of the toluene and residual 2-mercaptopropionic acid were removed by distillation under vacuum
  8. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-f6874f72fb8f4f17adcda0cfbd355085
Source dataset
uspto-grants-2007_07
Patent number
US07250457B2

Reaction notes

Loading…