Methanethiol → 3-(4-Methoxybenzylmercapto)-2-(methylthio)propanoic acid

HRID 262715Notes

Reaction equation

HRID 262715 reaction equation
Br[CH:2]([CH2:6][S:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].[CH3:17][SH:18].[OH-].[Na+]>C(O)C>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][S:7][CH2:6][CH:2]([S:18][CH3:17])[C:3]([OH:5])=[O:4])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 14798Sodium HydroxideHCID 203852902-Bromo-3-(4-methoxybenzylmercapto)propanoic acid

Product 1

HCID 540570183-(4-Methoxybenzylmercapto)-2-(methylthio)propanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-3-(4-methoxybenzylmercapto) propanoic acid (15 g.), methylmercaptan (3 g.) and sodium hydroxide(4.6 g.) in 95% ethanol (25 ml.) is refluxed for twelve hours. The sodium brimide is filtered off and the filtrate is concentrated to dryness in vacuo. The residue is dissolved in water, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer is dried and concentrated to dryness to yield 3-(4-methoxybenzylmercapto)-2-(methylthio)propanoic acid.

Workup

  1. filtrationThe sodium brimide is filtered off
  2. concentrationthe filtrate is concentrated to dryness in vacuo
  3. dissolutionThe residue is dissolved in water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer is dried
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f6963a6f4bda4be592e0d01671668b0f
Source dataset
uspto-grants-1979_05
Patent number
US04154936

Reaction notes

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