Benzoic Acid → Benzenecarbodithioic acid, propyl ester

HRID 990263Notes

Reaction equation

HRID 990263 reaction equation
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([SH:13])[CH2:11][CH3:12].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:15]>C1(C)C=CC=CC=1>[C:1]([S:13][CH2:10][CH2:11][CH3:12])(=[S:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 7848Propyl mercaptanHCID 14817Phosphorus sulfide (P2S5)

Product 1

HCID 578124Benzenecarbodithioic acid, propyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of benzoic acid (1.22 g), 1-propanethiol (0.76 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 single compound, propyl dithiobenzoate (1.21 g, 62%). It was further characterized 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-486ac90985ab4ba2bbe6d82ed5d8b89c
Source dataset
uspto-grants-2002_10
Patent number
US06458968B2

Reaction notes

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