Lithium hydroxide, monohydrate → HCID 53929988, compound

HRID 341740Notes

Reaction equation

HRID 341740 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([O:12][CH3:13])[C:3]=1[S:14][CH3:15].O.[OH-].[Li+]>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[C:3]=1[S:14][CH3:15]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53676987HCID 53676987, compound

Product 1

HCID 53929988HCID 53929988, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-chloro-2-methoxy-3-(methylsulphenyl)benzoate (85% pure, 16.9 g) and lithium hydroxide monohydrate (3.85 g) in aqueous methanol was stirred at room temperature overnight. The mixture was evaporated then treated with water and acidified to pH1. It was extracted with ethyl acetate, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 4-chloro-2-methoxy-3-(methylsulphenyl)benzoic acid (14.7 g) as a white solid m.p. 121.3°-122.7° C. NMR (CDCl3) 2.45(s,3H), 4.05(s,3H), 7.3(d.1H), 7.95(d,1H) containing only a trace of 4-chloro-3-(choromethylsulphenyl)-2-methoxybenzoic acid (determined by NMR).

Workup

  1. customThe mixture was evaporated
  2. additionthen treated with water
  3. extractionIt was extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-8f96a59bede148bc9ce3f8ed6634d6b2
Source dataset
uspto-grants-1999_01
Patent number
US05856274

Reaction notes

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