Sodium Hydroxide → 632366-11-1

HRID 270975Notes

Reaction equation

HRID 270975 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>O1CCCC1.CO>[F:18][C:17]([F:19])([F:20])[C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15036760Methyl 4-[3-(trifluoromethyl)phenoxy]benzoate

Product 1

HCID 18445868632366-11-1Yield 89.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3.56 g (12 mmol) of 4-(3-trifluoromethyl-phenoxy)-benzoic acid methyl ester, and 15 mL (60 mmol) of 4 N sodium hydroxide (NaOH) solution in 45 mL of tetrahydrofuran (THF) and 15 mL of methanol (MeOH) was heated at 50° C. for 25 h, when analysis by thin layer chromatography revealed complete conversion of starting material to product. The reaction mixture was concentrated and acidified with 2N HCl solution while keeping the flask in an ice bath, when a white precipitate formed. The solid was filtered and dried to give 3.02 g (89%) of desired 4-(3-trifluoromethyl-phenoxy)-benzoic acid as a white solid as indicated by 1H NMR and 19F-NMR.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwhen a white precipitate formed
  3. filtrationThe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-c16bd50d8ef64d02a2bd7e862706d722
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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