Piperidine → Butanoic acid, 3-[(4-methoxyphenyl)thio]-3-methyl-

HRID 2213550Notes

Reaction equation

HRID 2213550 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([OH:6])=[O:5].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1.N1CCCCC1>C(OCC)(=O)C>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:2]([CH3:7])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 109313-Methyl-2-butenoic acidHCID 127654-Methoxybenzenethiol

Product 1

HCID 10171427Butanoic acid, 3-[(4-methoxyphenyl)thio]-3-methyl-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

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 105° C. for 32 hours, cooled to room temperature and dissolved in ethyl acetate (EtOAc) (700mL). The resulting solution was washed with 1M 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 (3H, s), 2.54 (2H, s), 1.40 (6H, s).

Workup

  1. customA heavy-walled screw cap tube
  2. temperaturecooled to room temperature
  3. washThe resulting solution was washed with 1M aqueous HCl, H2O, and saturated aqueous NaCl
  4. dry with materialbefore being dried over Na2SO4
  5. customConcentration of the dry solution under reduced pressure afforded an oil which
  6. customprovided a crystalline solid

Sources & evidence

ORD record
ord-8a6a24969dae4b90919efad6e757507f
Source dataset
uspto-grants-2006_09
Patent number
US07105566B2

Reaction notes

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