Methanethiol → 2,3-Bis(methylsulphenyl)-4-chlorobenzoic acid

HRID 341731Notes

Reaction equation

HRID 341731 reaction equation
O.[OH-].[Li+].[CH3:4][SH:5].[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([S:16][CH3:17])[C:8]=1F.O>CN(C)C=O>[CH3:17][S:16][C:9]1[C:8]([S:5][CH3:4])=[C:7]([Cl:6])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 152187374-Chloro-3-fluoro-2-methylsulphenylbenzoic acid

Product 1

HCID 538155792,3-Bis(methylsulphenyl)-4-chlorobenzoic acidYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Lithium hydroxide monohydrate (4.95 g) was added to a solution of methyl mercaptan (4.4 g) in N,N-dimethyl formamide, and 4-chloro-3-fluoro-2-(methylsulphenyl)benzoic acid (5.5 g) was added to the resultant mixture. It was stirred at room temperature for 1 hour and heated to 80° C. overnight. It was cooled, poured into water, extracted with ether, washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography eluted with a mixture of acetic acid, ether and hexane (1:10:89) to give 2,3-bis(methylsulphenyl)-4-chlorobenzoic acid (3.24 g) as an off white solid, m.p. 130°-131° C.

Workup

  1. temperatureheated to 80° C. overnight
  2. temperatureIt was cooled
  3. extractionextracted with ether
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by column chromatography
  9. washeluted with a mixture of acetic acid, ether and hexane (1:10:89)

Sources & evidence

ORD record
ord-f8954694ed174ff799bece52afb1517e
Source dataset
uspto-grants-1999_01
Patent number
US05856274

Reaction notes

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