Thioglycolic Acid → HCID 131736111, compound

HRID 1052329Notes

Reaction equation

HRID 1052329 reaction equation
[CH2:1]1[O:5][C@@H:4]2[C@@H:6]([OH:9])[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[SH:11][CH2:12][C:13]([OH:15])=O.C[S:17](O)(=O)=O>C1(C)C=CC=CC=1>[CH2:1]1[O:5][C@@H:4]2[C@@H:6]([OH:9])[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[C:12]([S-:11])(=[S:17])[CH2:13][OH:15]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 6395Methanesulfonic AcidHCID 12597Isosorbide

Product 1

HCID 131736111HCID 131736111, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of isosorbide (60.00 grams, 0.41 moles), mercaptoacetic acid (83.21 grams, 0.90 moles), toluene (300 mL), and methane sulfonic acid (1.00 grams, 10 mmoles) was heated to reflux. Water was separated from the toluene/water azeotrope using a Dean Stark distillation trap. After four hours at reflux, a total of 15 mL of water was collected in the trap. The reaction mixture was cooled and washed with saturated aqueous sodium bicarbonate (2×200 mL) and brine (100 mL). The solution was dried over magnesium sulfate and then concentrated under reduced pressure. The product was a colorless oil. (Yield: 106.10 grams).

Workup

  1. temperaturewas heated to reflux
  2. customWater was separated from the toluene/water
  3. distillationa Dean Stark distillation trap
  4. temperatureAfter four hours at reflux
  5. customa total of 15 mL of water was collected in the trap
  6. temperatureThe reaction mixture was cooled
  7. washwashed with saturated aqueous sodium bicarbonate (2×200 mL) and brine (100 mL)
  8. dry with materialThe solution was dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8fce541236f14f879dcb38b3b08bb739
Source dataset
uspto-grants-2016_07
Patent number
US09388274B2

Reaction notes

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