Hydrochloric Acid → 4,4,4-Trifluorocrotonic acid

HRID 1004069Notes

Reaction equation

HRID 1004069 reaction equation
[F:1][C:2]([F:11])([F:10])/[CH:3]=[CH:4]/[C:5]([O:7]CC)=[O:6].[OH-].[Na+].Cl>C1COCC1>[F:1][C:2]([F:11])([F:10])/[CH:3]=[CH:4]/[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

Product 1

HCID 57096144,4,4-Trifluorocrotonic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4,4,4-trifluorocrotonate (9.85g, 65.9 mmole) and 1N NaOH (92.3 mL, 92.3 mmole) in THF (24 mL) was stirred at room temperature for 3 hours. The pH was brought to 1 with conc. HCl and the mixture extracted with Et2O (3×). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the title compound as an oil. NMR (CDCl3): δ 6.55 (d, 1H); 6.89 (dq, 1H).

Workup

  1. extractionthe mixture extracted with Et2O (3×)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5126107b1ce149e9bbbb292fa768572a
Source dataset
uspto-grants-2000_04
Patent number
US06048869

Reaction notes

Loading…