Thioglycolic Acid → [{1-(6-Methyl-1,3-benzodioxol-5-yl)propyl}thio]acetic acid

HRID 486951Notes

Reaction equation

HRID 486951 reaction equation
[CH3:1][C:2]1[C:3]([CH:11](O)[CH2:12][CH3:13])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[SH:15][CH2:16][C:17]([OH:19])=[O:18]>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][C:2]1[C:3]([CH:11]([S:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:12][CH3:13])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

5

Reactant 2

HCID 1133Thioglycolic AcidHCID 145148971-(6-Methylbenzo[d][1,3]dioxol-5-yl)propan-1-ol

Product 1

HCID 14514911[{1-(6-Methyl-1,3-benzodioxol-5-yl)propyl}thio]acetic acidYield 90.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

2.27 g of 1-(6-methyl-1,3-benzodioxol-5-yl)-1-propanol, 0.1 g of p-toluenesulfonic acid and 1.52 g of mercaptoacetic acid were dissolved in 80 ml of benzene to obtain a solution. This solution was heated under reflux for 12 hours, while removing generated water. The reaction mixture was poured into water. The aqueous layer was basified and washed with ether. The aqueous layer was acidified and extracted with chloroform. The organic layer was washed with water, dried over magnesium sulfate and concentrated in a vacuum to obtain a pale yellow solid. This solid was purified by silica gel column chromatography (ethyl acetate/hexane=2:8) to obtain 2.83 g of the title compound as a white crystal.

Workup

  1. customto obtain a solution
  2. temperatureThis solution was heated
  3. temperatureunder reflux for 12 hours
  4. customwhile removing
  5. additionThe reaction mixture was poured into water
  6. washwashed with ether
  7. extractionextracted with chloroform
  8. washThe organic layer was washed with water
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated in a vacuum
  11. customto obtain a pale yellow solid
  12. customThis solid was purified by silica gel column chromatography (ethyl acetate/hexane=2:8)

Sources & evidence

ORD record
ord-75705dd5e4e64dfabc0404011fd65e95
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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