Sodium Hydroxide → HCID 18444740, compound

HRID 912550Notes

Reaction equation

HRID 912550 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[C:9]([F:10])=[C:8]([O:11][CH3:12])[CH:7]=[C:6]([O:13][CH3:14])[C:5]=1[Cl:15].[OH-].[Na+]>C(O)C>[Cl:15][C:5]1[C:6]([O:13][CH3:14])=[CH:7][C:8]([O:11][CH3:12])=[C:9]([F:10])[C:4]=1[C:3]([OH:16])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59486265HCID 59486265, compound

Product 1

HCID 18444740HCID 18444740, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-chloro-6-fluoro-3,5-dimethoxy-benzoic acid methyl ester (7.9 g, 31.9 mmol) and sodium hydroxide (3.2 g, 79.6 mmol) in 96 mL of anhydrous ethanol is refluxed for 24 hours. The ethanol is concentrated in vacuo and solid residue is dissolved in water and extracted twice with ether. The aqueous layer is acidified with Conc. HCl and a white precipitate is filtered, washed with cold water and dried in vacuo to afford 2-chloro-6-fluoro-3,5-dimethoxy-benzoic acid (21); 1H NMR 400 MHz (CDCl3) δ 6.61 (d, 1H), 3.87 (s, 3H), 3.84 (s, 3H); MS m/z 235.0 (M+1).

Workup

  1. temperatureis refluxed for 24 hours
  2. concentrationThe ethanol is concentrated in vacuo and solid residue
  3. dissolutionis dissolved in water
  4. extractionextracted twice with ether
  5. filtrationa white precipitate is filtered
  6. washwashed with cold water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d8390697cf204768855408dcc70a55c0
Source dataset
uspto-grants-2011_09
Patent number
US08026243B2

Reaction notes

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