Toluene → Methyl 2,5-bis(2,2,2-trifluoroethoxy)benzoate

HRID 460427

Reaction equation

HRID 460427 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[C:26]1(C)C=CC=CC=1>CO>[F:1][C:2]([F:20])([F:21])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:10][C:6]=1[C:7]([O:9][CH3:26])=[O:8]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 27360782,5-bis(2,2,2-trifluoroethoxy)benzoic Acid

Product 1

HCID 2727094Methyl 2,5-bis(2,2,2-trifluoroethoxy)benzoateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,5-bis(2,2,2-trifluoroethoxy)benzoic acid (20 g) and thionyl chloride (15.0 g) in methanol (100 ml) was stirred at 80° C. for 2 hours. The solvents were evaporated under vacuum to give an oil residue. Toluene (100 ml) was added to the residue and the solution was washed with saturated NaHCO3 (30 ml) solution followed by water (3×30 ml). The organic layer was concentrated under reduced pressure to give the product as a white solid (20.5 g, yield 98.0%).

Workup

  1. customThe solvents were evaporated under vacuum
  2. customto give an oil residue
  3. washthe solution was washed with saturated NaHCO3 (30 ml) solution
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8a2a5e9993e74072941f4e4b4d260e81
Source dataset
uspto-grants-2007_03
Patent number
US07196197B2

Linked notes

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