Hydrochloric Acid → HCID 54252146, compound

HRID 1740598Notes

Reaction equation

HRID 1740598 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[CH2:15][C:16]([O:18]C)=[O:17].O.[Li+].[OH-].Cl>C1COCC1>[F:1][C:2]([F:20])([F:21])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:6]=1[CH2:15][C:16]([OH:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 53872034HCID 53872034, compound

Product 1

HCID 54252146HCID 54252146, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 2-(2,2,2-trifluoroethoxy)-5-trifluoromethylphenylacetate (1.07 g, 3.5 mmol) from Step 2 above in THF (8 mL) and water (2 mL) was added LiOH (0.20 g, 4.8 mmol). The mixture was stirred at ambient temperature for 24 h. The reaction was acidified to pH 2 with 5 N aqueous HCl and the solvents were removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using a gradient elution of 0-50% MeOH:CH2Cl2 to give 2-(2,2,2-trifluoroethoxy)-5-trifluoromethylphenylacetic acid as a gum (HPLC retention time=8.7 min (method A)).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was purified by pressurized silica gel column chromatography
  3. washa gradient elution of 0-50% MeOH

Sources & evidence

ORD record
ord-36b08cba318c4070a7fab5a85d448d33
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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