Propionic Acid → HCID 14025552, compound

HRID 990264Notes

Reaction equation

HRID 990264 reaction equation
[C:1](O)(=O)[CH2:2][CH3:3].[CH2:6]([SH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:15]>C1(C)C=CC=CC=1>[C:1]([S:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[S:15])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 7509Benzyl mercaptanHCID 14817Phosphorus sulfide (P2S5)

Product 1

HCID 14025552HCID 14025552, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of propionic acid (0.74 g), benzyl mercaptan (1.24 g) and phosphorus pentasulfide (4.44 g) in toluene (40 ml) was refluxed for 10 h. A dark red color was developed immediately after heating. After the reaction was complete (as monitored by GC-MS), it was cooled to room temperature and purified by a column chromatography packed with neutral alumina, eluting with benzene. Removal of the solvent by distillation gave the desired compound, benzyl dithiopropionate (0.98 g, 50%) without further purification. The structure was confirmed by 1H and 13C-NMR.

Workup

  1. temperaturewas refluxed for 10 h
  2. temperatureafter heating
  3. custompurified by a column chromatography
  4. washeluting with benzene
  5. customRemoval of the solvent
  6. distillationby distillation

Sources & evidence

ORD record
ord-bdfa2addd3f14a97b2b0487446373a0e
Source dataset
uspto-grants-2002_10
Patent number
US06458968B2

Reaction notes

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