3-(Trifluoromethyl)benzoic acid → HCID 20384619, compound

HRID 1076080Notes

Reaction equation

HRID 1076080 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.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22]>>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][C:19]([C:6]([C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:1])([F:13])[F:12])[CH:4]=2)=[O:8])=[CH:20][C:15]=1[CH3:14]

Participants

3

Reactant 2

HCID 99633-(Trifluoromethyl)benzoic acidHCID 336372-Methylanisole

Product 1

HCID 20384619HCID 20384619, compound

Conditions

Temperature
90 °C

Procedure

m-Trifluoromethylbenzoic acid (19.0g, 0.10 mole) and o-methylanisole(12.2g, 0.10 mole) are combined in 50 ml of polyphosphoric acid (PPA) and warmed with stirring to 90°C for 4.5 hours. The cooled reaction mixture is then poured into ice water and extracted into ethyl acetate (200 ml) to give, after extraction with 5% aqueous sodium hydroxide 15 g of product (53%), m.p. 56°-59°C, upon removal of the solvent in vacuo.

Workup

  1. temperaturewarmed
  2. customThe cooled reaction mixture
  3. extractionextracted into ethyl acetate (200 ml)
  4. customto give
  5. extractionafter extraction with 5% aqueous sodium hydroxide 15 g of product (53%), m.p. 56°-59°C
  6. customupon removal of the solvent in vacuo

Sources & evidence

ORD record
ord-2e644bc105694213b7f24010674c07ab
Source dataset
uspto-grants-1976_05
Patent number
US03954875

Reaction notes

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