Sodium Methoxide → Methyl 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate

HRID 215716Notes

Reaction equation

HRID 215716 reaction equation
F[C:2]1[C:11]([S:12][CH3:13])=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:18][O-:19].[Na+]>CO>[CH3:18][O:19][C:2]1[C:11]([S:12][CH3:13])=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 66959475HCID 66959475, compound

Product 1

HCID 66959164Methyl 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoateYield 18.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 19.9 g (74.2 mmol) of methyl 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate and 40.1 g (30% by weight, 223 mmol) of sodium methoxide in 250 ml of methanol was heated under reflux for 6 h. For work-up, the mixture was concentrated on a rotary evaporator, the residue was taken up in water and the mixture was extracted with dichloromethane. The organic phase was dried and the filtrate was freed from the solvent. This gave 15.9 g of methyl 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate as residue. The aqueous phase from the extractive work-up was acidified with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was dried and the filtrate was freed from the solvent. This gave an additional 3.80 g of methyl 2-methoxy-3-methylthio-4-(trifluoromethyl)benzoate as residue.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 h
  3. concentrationFor work-up, the mixture was concentrated on a rotary evaporator
  4. extractionthe mixture was extracted with dichloromethane
  5. customThe organic phase was dried
  6. extractionextracted with ethyl acetate
  7. customThe organic phase was dried

Sources & evidence

ORD record
ord-912ba68d57b54d7b926afaffcb88c6da
Source dataset
uspto-grants-2012_06
Patent number
US08193121B2

Reaction notes

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