Thioglycolic Acid → HCID 86749150, compound

HRID 2259790Notes

Reaction equation

HRID 2259790 reaction equation
[CH:1]([C:4]1[C:5]([CH:13](O)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([CH3:3])[CH3:2].S[CH2:22][C:23]([OH:25])=[O:24].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:1]([C:4]1[C:5]([CH:13]([CH2:22][C:23]([OH:25])=[O:24])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 53784355HCID 53784355, compound

Product 1

HCID 86749150HCID 86749150, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

1.2 g of α-(6-isopropyl-1,3-benzodioxol-5-yl)-benzyl alcohol was dissolved in 10 ml of benzene, followed by the addition of 490 mg of mercaptoacetic acid and a catalytic amount of p-toluenesulfonic acid monohydrate. The obtained mixture was heated under reflux for one hour and cooled, followed by the addition of benzene. The mixture was washed with water, followed by the addition of a 1N aqueous solution of sodium hydroxide. The alkaline layer was separated, acidified with concentrated hydrochloric acid and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and filtered. The filtrate was distilled to remove the solvent. The residue was purified by silica gel column chromatography (hexane/chloroform=3:7) to obtain 1.42 g of the title compound as a colorless prismatic crystal.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for one hour
  3. temperaturecooled
  4. washThe mixture was washed with water
  5. additionfollowed by the addition of a 1N aqueous solution of sodium hydroxide
  6. customThe alkaline layer was separated
  7. extractionextracted with chloroform
  8. washThe extract was washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. distillationThe filtrate was distilled
  12. customto remove the solvent
  13. customThe residue was purified by silica gel column chromatography (hexane/chloroform=3:7)

Sources & evidence

ORD record
ord-024902cc59904fcaaef63412d1f26d7e
Source dataset
uspto-grants-1995_12
Patent number
US05475024

Reaction notes

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