Hydrochloric Acid → 3-[4-(Trifluoromethyl)phenyl]but-2-enoic acid

HRID 585974Notes

Reaction equation

HRID 585974 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[CH3:16])=[CH:10]/[C:11]([O:13]CC)=[O:12])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>CCO.[Cl-].[Na+].O>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:4]=[CH:5][C:6](/[C:9](/[CH3:16])=[CH:10]/[C:11]([OH:13])=[O:12])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69760751ethyl(2E)-3-[4-(trifluoromethyl)phenyl]-2-butenoate

Product 1

HCID 287914333-[4-(Trifluoromethyl)phenyl]but-2-enoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The product from Example 142A (3.5 g, 13.5 mmol) in EtOH (80 mL) was treated with aqueous 1M NaOH (40 mL) and stirred for 16 hours at ambient temperature. The reaction mixture was neutralized with 1N HCl (40 mL), diluted with brine, and extracted with diethyl ether to provide the title compound. NMR (CDCl3) 2.60 (s, 3H), 6.82 (s, 1H), 7.58 (d, 2H), 7.65 (d, 2H).

Workup

  1. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-60a5c92ab495413097d52d82e7f19861
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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