Sodium Hydroxide → 3-Fluoro-4-isobutylbenzoic acid

HRID 1443408Notes

Reaction equation

HRID 1443408 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH:13]([CH3:15])[CH3:14])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][CH:13]([CH3:15])[CH3:14])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54062470Methyl 3-fluoro-4-isobutylbenzoate

Product 1

HCID 638867323-Fluoro-4-isobutylbenzoic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 3-fluoro-4-isobutylbenzoate (243 mg, 1.16 mmol) in 10 mL of EtOH was added sodium hydroxide (2.3 mL, 5.0 N). The mixture was stirred at rt for 1 hr and then concentrated. The residue was partitioned in a mixture of diluted HCl (10 mL) and Et2O (10 mL). The aqueous layer was separated and further extracted with Et2O (2×10 mL). The organic layers were combined, dried over MgSO4, and concentrated to give 212 mg (93%) of the title compound: 1H NMR δ 0.93 (d, J=6.6, 6H), 1.95 (m, 1H), 2.58 (d, J=7.4, 2H), 7.26 (m, 1H), 7.74 (dd, J=1.4, 10.1, 11H), 7.82 (dd, J=1.5, 7.9, 11H), 11.2 (br. s, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned in a mixture of diluted HCl (10 mL) and Et2O (10 mL)
  3. customThe aqueous layer was separated
  4. extractionfurther extracted with Et2O (2×10 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dcd8e22e59f649f9bc622cf1b6a5da63
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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