4-Methoxybenzoic Acid → Benzyl 4-methoxybenzene-1-carbodithioate

HRID 990258Notes

Reaction equation

HRID 990258 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=O)=[CH:5][CH:4]=1.[CH2:12]([SH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>C1(C)C=CC=CC=1>[CH2:12]([S:19][C:7](=[S:21])[C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 74784-Methoxybenzoic AcidHCID 7509Benzyl mercaptanHCID 14817Phosphorus sulfide (P2S5)

Product 1

HCID 13359578Benzyl 4-methoxybenzene-1-carbodithioateYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-methoxybenzoic acid (1.52 g), benzyl mercaptan (1.24 g) and phosphorus pentasulfide (4.44 g) in toluene (40 ml) was refluxed for 12 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, benzyl-4-methoxydithiobenzoate (1.89 g, 69%). It was further characterized by 1H and 13C-NMR.

Workup

  1. temperaturewas refluxed for 12 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-3bf29329859f47259f41de34381d4ae9
Source dataset
uspto-grants-2002_10
Patent number
US06458968B2

Reaction notes

Loading…