Reaction #1005974

Reaction equation

3-methyl-2-butenoic acid

4-methoxy thiophenol

piperidine

→

3-(4-methoxy-phenylsulfanyl)-3-methyl-butyric acid

Solvents

EtOAc

Conditions

Workup

1. 1
   OtherA heavy-walled screw cap tube
2. 2
   Temperaturecooled to room temperature
3. 3
   WashThe resulting solution was washed with 1 M aqueous HCl, H2O, and saturated aqueous NaCl
4. 4
   Dryingbefore being dried over Na2SO4
5. 5
   OtherConcentration of the dry solution under reduced pressure afforded an oil which
6. 6
   Otherprovided a crystalline solid

Procedure

A heavy-walled screw cap tube was charged with 3-methyl-2-butenoic acid (13.86 g, 138.4 mmol), 4-methoxy thiophenol (20.0 g, 138.4 mmol), and piperidine (3.45 g, 41.6 mmol). This mixture was heated to 10° C. for 32 hours, cooled to room temperature and dissolved in EtOAc (700 mL). The resulting solution was washed with 1 M aqueous HCl, H2O, and saturated aqueous NaCl before being dried over Na2SO4. Concentration of the dry solution under reduced pressure afforded an oil which upon standing in the freezer provided a crystalline solid. 3-(4-methoxy-phenylsulfanyl)-3-methyl-butyric acid was isolated as pale-yellow crystals by washing the crystalline solid with pentane. (27.33 g, 82%). 1H NMR (300 MHz, CDCl3) δ: 7.48 (2H, d, J=9.0 Hz), 6.89 (2H, d, J=8.9 Hz), 3.83 is (3H, s), 2.54 (2H, s), 1.40 (6H, s).

Source