Methanol → Methyl 3-(trifluoromethyl)benzoate

HRID 2409810

Reaction equation

HRID 2409810 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].S(Cl)(Cl)=O.[CH3:18]O>>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:8][CH3:18])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 99633-(Trifluoromethyl)benzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 520213Methyl 3-(trifluoromethyl)benzoateYield 86%

Conditions

Temperature
75 °C

Procedure

To a solution of 3-(trifluoromethyl)benzoic acid (5 g, 26.30 mmol, 1.00 equiv) in methanol (25 mL) was added dropwise thionyl chloride (9.39 g, 78.93 mmol, 3.00 equiv) and the resulting solution was stirred for 2 h at 75° C. in an oil bath. The mixture was concentrated under vacuum, diluted with 100 mL of ethyl acetate and then washed with 2×30 mL of sodium carbonate and 2×30 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to yield 4.6 g (86%) of methyl 3-(trifluoromethyl)benzoate as yellow oil

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additiondiluted with 100 mL of ethyl acetate
  3. washwashed with 2×30 mL of sodium carbonate and 2×30 mL of brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a925cda08c1444a48091a1c05307e595
Source dataset
uspto-grants-2014_08
Patent number
US08815910B2

Linked notes

Loading…