Methacrylic Acid → 3-[(4-Methoxyphenyl)methylthio]-2-methylpropanoic acid

HRID 262574Notes

Reaction equation

HRID 262574 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][SH:10])=[CH:5][CH:4]=1.[C:11]([OH:16])(=[O:15])[C:12]([CH3:14])=[CH2:13].[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][CH2:13][CH:12]([CH3:14])[C:11]([OH:16])=[O:15])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 4093Methacrylic AcidHCID 14798Sodium HydroxideHCID 804074-Methoxy-alpha-toluenethiol

Product 1

HCID 132083193-[(4-Methoxyphenyl)methylthio]-2-methylpropanoic acid

Procedure

p-Methoxy-α-toluene thiol (15.4 g., 0.1 mol.) is added to a solution of methacrylic acid (8.6 g., 0.1 mol.) in 50 ml. 2 N sodium hydroxide. The mixture is heated on the steam bath for three hours, then refluxed for two hours and cooled. The mixture is extracted with ether, then the aqueous layer is acidified with concentrated HCl and extracted with dichloromethane. The acidic extracts are washed with brine, dried (MgSO4) and evaporated in vacuo. The resulting semi-solid is taken up in 50 ml. of dichloromethane, diluted with 50 ml. hexane, and chilled. 3-[(4-methoxyphenyl)methylthio]-2-methylpropanoic acid is collected as a white crystalline solid, m.p. 74°-82° (5.5 g.).

Workup

  1. temperatureThe mixture is heated on the steam bath for three hours
  2. temperaturerefluxed for two hours
  3. temperaturecooled
  4. extractionThe mixture is extracted with ether
  5. extractionextracted with dichloromethane
  6. washThe acidic extracts are washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo
  9. additionof dichloromethane, diluted with 50 ml
  10. temperaturehexane, and chilled
  11. custom3-[(4-methoxyphenyl)methylthio]-2-methylpropanoic acid is collected as a white crystalline solid, m.p. 74°-82° (5.5 g.)

Sources & evidence

ORD record
ord-1074253ab38d490b9ae12bc1364e7574
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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