Thioglycolic Acid → HCID 178526155, compound

HRID 1898955Notes

Reaction equation

HRID 1898955 reaction equation
O[CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C(O)(=O)C[SH:18].[C:21]([O:24]CC)(=O)[CH3:22]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH:14]1[C:15]2[CH:2]([CH2:22][C:21]([OH:24])=[S:18])[C:3]3[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=3)[O:9][C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 1133Thioglycolic AcidHCID 8857Ethyl AcetateHCID 72861Xanthydrol

Product 1

HCID 178526155HCID 178526155, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A solution of 9-hydroxyxanthene (Aldrich) (1.0 g, 5.0 mmol), thioglycolic acid (42 μL, 6.0 mmol), and ρ-toluenesulfonic acid monohydrate (10 mg) in 10 mL of toluene is stirred for 30 minutes. The reaction is diluted with ethyl acetate and washed 3 times with water and once with brine. The organic phase is dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting solid is chromatographed twice on silica gel eluting with methanol:chloroform (5:95) to give 1.0 g (72%) of xanthen-9-yl-thioacetic acid: melting point 131°-132° C.

Workup

  1. washwashed 3 times with water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting solid is chromatographed twice on silica gel eluting with methanol:chloroform (5:95)

Sources & evidence

ORD record
ord-90c4f0e64509419a9cd9f43efd70f800
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

Loading…