Methanol → Methyl 4-chloro-3-(trifluoromethyl)benzoate

HRID 62789Notes

Reaction equation

HRID 62789 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH3:15]O.S(=O)(=O)(O)O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:15])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27738574-Chloro-3-(trifluoromethyl)benzoic acid

Product 1

HCID 14148738Methyl 4-chloro-3-(trifluoromethyl)benzoateYield 92.7%

Procedure

To a solution of 4-chloro-3-(trifluoromethyl)benzoic acid (200 g, 891 mmol) in MeOH (600 mL, 14.8 mol), sulfuric acid (27 mL, 445 mmol) was added. The mixture was stirred at reflux for 6 h, allowed to cool and the solvent evaporated under reduce pressure. The resulting liquid residue (˜250 mL) was poured onto ice water whereby a white suspension formed. The solid was filtered and washed with 0.05 N NaOH (3×200 mL) followed by H2O (3×200 mL). The solid was dried under vacuum for 16 h followed by 4 h at 40° C. to give the title compound as an off-white solid (197.0 g). 1H NMR (400 MHz, CDCl3) δ ppm, 3.98 (s, 3H), 7.62 (d, J=8.4 Hz, 1H), 8.16 (dd, J=8.8 Hz, 2.0 Hz, 1H), 8.39 (d, J=2.0 Hz, 1H).

Workup

  1. temperatureat reflux for 6 h
  2. temperatureto cool
  3. customthe solvent evaporated
  4. additionThe resulting liquid residue (˜250 mL) was poured onto ice water whereby a white suspension
  5. customformed
  6. filtrationThe solid was filtered
  7. washwashed with 0.05 N NaOH (3×200 mL)
  8. customThe solid was dried under vacuum for 16 h

Sources & evidence

ORD record
ord-f7cf84864ec24a7daa42f930647b3e0c
Source dataset
uspto-grants-2016_09
Patent number
US09447041B2

Reaction notes

Loading…