Methanol → 3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid methyl ester

HRID 437493

Reaction equation

HRID 437493 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9].[CH3:22]O>>[Cl:1][C:2]1[CH:17]=[C:16]([C:18]([F:20])([F:19])[F:21])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH3:22])=[O:9]

Participants

3

Reactant 2

HCID 887MethanolHCID 916853-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

Product 1

HCID 134206893-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid methyl esterYield 98%

Conditions

Temperature
50 °C

Procedure

To a 300 ml, 3-necked flask equipped with a stirrer, gas bubbling tube, condenser, thermometer and drying tube is charged anhydrous methanol (100 ml) and 3-(2-chloro-4-trifluoromethylphenoxy)benzoic acid (12 g., 0.038 mole). Anhydrous hydrogen chloride gas is bubbled into the reaction mixture until the reaction temperature (exotherm) rises to 50° C. The reaction mixture is then maintained at 50° C. with external heating for 4 hours, then cooled, the solvent removed in vacuo and the residue dissolved in CCl4 (200 ml) and triturated with water (50 ml). The decanted and dried (anh. MgSO4) CCl4 layer is reduced in vacuo to give 12.2 g. of methyl 3-(2-chloro-4-trifluoromethylphenoxy)benzoate (98% yield).

Workup

  1. customTo a 300 ml, 3-necked flask equipped with a stirrer
  2. customgas bubbling tube, condenser
  3. customthermometer and drying tube
  4. customAnhydrous hydrogen chloride gas is bubbled into the reaction mixture until the reaction temperature (exotherm)
  5. customrises to 50° C
  6. temperaturewith external heating for 4 hours
  7. temperaturecooled
  8. customthe solvent removed in vacuo
  9. dissolutionthe residue dissolved in CCl4 (200 ml)
  10. customtriturated with water (50 ml)
  11. customThe decanted
  12. dry with materialdried (anh. MgSO4) CCl4 layer
  13. customto give 12.2 g

Sources & evidence

ORD record
ord-934a86f90d964f338bc5f3d4af4a7a79
Source dataset
uspto-grants-1977_06
Patent number
US04031131

Linked notes

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