Sodium Hydroxide → 3-Fluoro-4-isopropoxybenzoic acid

HRID 2204202Notes

Reaction equation

HRID 2204202 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:15])[CH3:14])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58551191Methyl 3-fluoro-4-isopropoxybenzoate

Product 1

HCID 179028843-Fluoro-4-isopropoxybenzoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-fluoro-4-isopropoxybenzoate (from step 1), 1,4-dioxane (31 mL), and NaOH (31 mL of 1.0 M, 31 mmol) were combined and the mixture was heated at 80° C. for 20 min. The solvent was evaporated under reduced pressure. The crude mixture was dissolved in water and was washed with EtOAc (3×). The combined organics were discarded. The aqueous layer was acidified and was extracted with EtOAc (3×). The organic layer was dried over sodium sulfate, filtered and the concentrated under reduced pressure to yield 3-fluoro-4-isopropoxy-benzoic acid (1.25 g, 72%) as a white solid. ESI-MS m/z calc 198.1, found 199.3 (M+1)+. Retention time: 1.34 minutes (3 min run).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe crude mixture was dissolved in water
  3. washwas washed with EtOAc (3×)
  4. extractionwas extracted with EtOAc (3×)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe concentrated under reduced pressure

Sources & evidence

ORD record
ord-2d96be941cf140e1bbf3e9f2d4020121
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

Loading…