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

HRID 1059744Notes

Reaction equation

HRID 1059744 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>CCOC(C)=O>[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 EtOAc (700 mL). 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-d6301432a91b4f3492617108b98a34fa
Source dataset
uspto-grants-2003_02
Patent number
US06521641B1

Reaction notes

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