Hydrochloric Acid → 4-[4-(Trifluoromethyl)phenyl]phenylacetic acid

HRID 1669286Notes

Reaction equation

HRID 1669286 reaction equation
Cl.[F:2][C:3]([F:20])([F:19])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13](CC#N)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[OH-:21].[Na+].[O:23]1[CH2:28][CH2:27]OCC1>>[F:2][C:3]([F:20])([F:19])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:27][C:28]([OH:23])=[O:21])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 20099836[4'-(Trifluoromethyl)[1,1'-biphenyl]-4-yl] acetonitrile

Product 1

HCID 222801814-[4-(Trifluoromethyl)phenyl]phenylacetic acidYield 90%

Conditions

Temperature
110 °C

Procedure

Concentrated hydrochloric acid (37%, 1 mL) is added to a solution of (4′-trifluoromethyl-biphenyl-4-yl)-acetonitrile (0.290 g, 1.11 mmol) in [1,4]dioxane (2 mL), heated at 110° C. for six hours, cooled to room temperature and adjust pH to 3 using 5.0 N sodium hydroxide, extracted with ethyl acetate three times. Organics are dried over sodium sulfate, filtered and concentrated to provide 0.280 g (11.0 mmol, 90%) of title compound.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate three times
  3. dry with materialOrganics are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b79df3a876d34636a3252025c453456b
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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