HCID 66739997, compound → 2-(4-Fluoro-3-methoxyphenyl)-2-methylpropanoic acid

HRID 1627344Notes

Reaction equation

HRID 1627344 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=[O:10])=[CH:4][C:3]=1[O:15][CH3:16]>CO.[OH-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[O:15][CH3:16]

Participants

5

Reactant 1

HCID 66739997HCID 66739997, compound

Product 1

HCID 667406012-(4-Fluoro-3-methoxyphenyl)-2-methylpropanoic acidYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 2-(4-fluoro-3-methoxyphenyl)-2-methylpropanoate (146 g) in MeOH (2 L) and 25% NaOH in H2O (590 mL) was heated at reflux for 5 h. The reaction mixture was then allowed to cool to room temperature and concentrated at reduced pressure. The residue was dissolved in H2O (2 L) and washed with ether (500 mL). The aqueous layer was acidified cautiously with conc HCl to pH 2. The resulting mixture was extracted with DCM (3 L), and combined extracts were dried over MgSO4, and concentrated at reduced pressure to give 2-(4-fluoro-3-methoxyphenyl)-2-methylpropanoic acid (95 g, 84% over 2 steps). 1H NMR (400 MHz, CDCl3): δ 7.06-7.00 (m, 2H), 6.93 (m, 1H), 3.90 (s, 3H), 3.86 (s, 2H), 1.60 (s, 6H).

Workup

  1. temperatureat reflux for 5 h
  2. concentrationconcentrated at reduced pressure
  3. dissolutionThe residue was dissolved in H2O (2 L)
  4. washwashed with ether (500 mL)
  5. extractionThe resulting mixture was extracted with DCM (3 L)
  6. dry with materialwere dried over MgSO4
  7. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-347099375e52460388294b7681c4ad2a
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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