Hydrochloric Acid → 3-(Phenylthio)propanoic acid

HRID 1009209Notes

Reaction equation

HRID 1009209 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:15]([OH:19])(=[O:18])[CH:16]=[CH2:17].Cl>C1COCC1>[C:1]1([S:7][CH2:17][CH2:16][C:15]([OH:19])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6581Acrylic AcidHCID 7969ThiophenolHCID 8471Triethylamine

Product 1

HCID 2224923-(Phenylthio)propanoic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of thiophenol (8.87 g, 80.6 mmol) in THF (20 ml) and triethylamine (8.6 g, 11.9 ml, 85 mmol) was added dropwise, with ice cooling, acrylic acid (5.8 g, 5.5 ml, 81 mmol). The reaction mixture was stirred at 0° C. for 1 h and then at RT overnight, acidified with 2N hydrochloric acid and extracted with diethyl ether (2×100 ml). The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. The desired 3-phenylsulfanylpropionic acid product (13.67 g, 93% of theory) was obtained as a white solid (m.p. 51-54° C.)

Workup

  1. customat RT
  2. customovernight
  3. extractionextracted with diethyl ether (2×100 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-209a8d69d1fb479c965c0b003775adc6
Source dataset
uspto-grants-2011_07
Patent number
US07973072B2

Reaction notes

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