Benzoic Acid → Benzyl dithiobenzoate

HRID 990257Notes

Reaction equation

HRID 990257 reaction equation
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([SH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19]>C1(C)C=CC=CC=1>[C:1]([S:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[S:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 7509Benzyl mercaptanHCID 14817Phosphorus sulfide (P2S5)

Product 1

HCID 11459208Benzyl dithiobenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of benzoic acid (1.22 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 column chromatography packed with.neutral alumina, eluting with benzene. Removal of the solvent by distillation gave the single compound, benzyl dithiobenzoate (2.22 g, 91%). It was further characterized by 1H and 13C-NMR.

Workup

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

Sources & evidence

ORD record
ord-26115d13a3024401b498fe143ffdb59f
Source dataset
uspto-grants-2002_10
Patent number
US06458968B2

Reaction notes

Loading…