Hydrochloric Acid → HCID 66817651, compound

HRID 1755097Notes

Reaction equation

HRID 1755097 reaction equation
C([O:5][C:6](=[O:22])[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([O:17][CH2:18][CH2:19][CH:20]=[CH2:21])[CH:8]=1)CC=C.[OH-].[Na+].Cl>CO>[CH2:18]([O:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=1)[C:6]([OH:22])=[O:5])[CH2:19][CH:20]=[CH2:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66817593HCID 66817593, compound

Product 1

HCID 66817651HCID 66817651, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-But-3-enyloxy-5-trifluoromethyl-benzoic acid but-3-enyl ester (2.64 g, 8.39 mmol) was dissolved in methanol. A 5 N aqueous sodium hydroxide solution (5.1 ml, 25.2 mmol) was added and the mixture was stirred at room temperature for two hours. The reaction solution was cooled, quenched with 2 N hydrochloric acid (20 ml, 40 mmol) and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3-but-3-enyloxy-5-trifluoromethyl-benzoic acid (2.13 g, 98%).

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-81d7d9abf03e4f6f941bf9ad47859983
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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