Hydrochloric Acid → (RS)-3-carboxy-4-(2-chloro-1,1,2-trifluoroethoxy)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

HRID 345116Notes

Reaction equation

HRID 345116 reaction equation
[C:1]([C:6]1[C:10]([O:11][C:12]([F:17])([F:16])[CH:13]([Cl:15])[F:14])=[CH:9][N:8]([C:18]2[C:23]([Cl:24])=[CH:22][C:21]([C:25]([F:28])([F:27])[F:26])=[CH:20][C:19]=2[Cl:29])[N:7]=1)([O:3]CC)=[O:2].[OH-].[Na+].CO.Cl>O>[C:1]([C:6]1[C:10]([O:11][C:12]([F:16])([F:17])[CH:13]([Cl:15])[F:14])=[CH:9][N:8]([C:18]2[C:23]([Cl:24])=[CH:22][C:21]([C:25]([F:26])([F:28])[F:27])=[CH:20][C:19]=2[Cl:29])[N:7]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 19993695(RS)-3-carboethoxy-4-(2-chloro-1,1,2-trifluoroethoxy)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

Product 1

HCID 19993690(RS)-3-carboxy-4-(2-chloro-1,1,2-trifluoroethoxy)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazoleYield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (RS)-3-carboethoxy-4-(2-chloro-1,1,2-trifluoroethoxy)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole 5 (0.95 g), aqueous sodium hydroxide solution (2M; 20 ml) and methanol (20 ml) was stirred at room temperature for 20 hours. The solution was acidified with hydrochloric acid (2M), diluted with water (50 ml) and extracted with ether (2×30 ml). The combined extracts were dried over magnesium sulfate and evaporated to give (RS)-3-carboxy-4-(2-chloro-1,1,2-trifluoroethoxy)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (0.7 g) as a yellow solid, m.p. 149°-159° C.

Workup

  1. extractionextracted with ether (2×30 ml)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-eaa6c786f7e04bb0853096cfcee2825a
Source dataset
uspto-grants-1991_10
Patent number
US05055482

Reaction notes

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