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

HRID 486897Notes

Reaction equation

HRID 486897 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].O>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

6

Reactant 3

HCID 962WaterHCID 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. The solution was heated under reflux for 12 h while water was removed. The reaction mixture was poured into water. The aqueous layer was made alkaline and washed with ether. The aqueous layer was then acidified and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to obtain a faint yellow solid. It was purified according to silica gel column chromatography (ethyl acetate/hexane=2:8) to obtain 2.83 g of the intended compound in the form of white crystals.

Workup

  1. temperatureThe solution was heated
  2. customwas removed
  3. additionThe reaction mixture was poured into water
  4. washwashed with ether
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a faint yellow solid
  10. customIt was purified

Sources & evidence

ORD record
ord-3867d52274ce4d4a96592bcccc868a12
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

Loading…