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

HRID 2419443Notes

Reaction equation

HRID 2419443 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. 2N sodium hydroxide. The mixture is heated on the steam bath for 3 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 3 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-4138e29bbbad44ad8887b79836880e7f
Source dataset
uspto-grants-1978_08
Patent number
US04105776

Reaction notes

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