Bromoacetic Acid → [{2-(1,3-Benzodioxol-5-yl)ethyl}thio]acetic acid

HRID 486903Notes

Reaction equation

HRID 486903 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][SH:12])=[CH:9][C:4]=2[O:3][CH2:2]1.Br[CH2:14][C:15]([OH:17])=[O:16].[OH-].[Na+]>C(O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 158195122-(1,3-Benzodioxol-5-yl)ethanethiol

Product 1

HCID 19001624[{2-(1,3-Benzodioxol-5-yl)ethyl}thio]acetic acidYield 93.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

100 g of 2-(1,3-benzodioxol-5-yl)ethanethiol and 75.1 g of bromoacetic acid were dissolved in 1 l of ethanol. A solution of 44 g of sodium hydroxide in 125 ml of water and then 2 l of ethanol were added thereto. The mixture was heated under reflux for 3 h. The reaction mixture was concentrated under reduced pressure. 2.5 l of water was added thereto. The mixture was made alkaline with a 1N sodium hydroxide solution, washed with 35% hydrochloric acid, extracted with ethyl acetate, washed with water four times and dried over sodium sulfate. The solvent was distilled off under reduced pressure to obtain 121 g of [{2-(1,3-benzodioxol-5-yl)ethyl}thio]acetic acid in the form of a faint yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. addition2.5 l of water was added
  5. washwashed with 35% hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. washwashed with water four times
  8. dry with materialdried over sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0c0e27bcb8b04d4695aa445e55300cd2
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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