Hydrochloric Acid → 2-(2,6-Difluoro-4-methoxyphenyl)malonic acid

HRID 82786Notes

Reaction equation

HRID 82786 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([F:12])[C:5]=1[CH:13]([C:19]([O:21]CC)=[O:20])[C:14]([O:16]CC)=[O:15].Cl>CCOCC>[F:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([F:12])[C:5]=1[CH:13]([C:19]([OH:21])=[O:20])[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11174138Diethyl 2-(2,6-difluoro-4-methoxyphenyl)malonate

Product 1

HCID 217064132-(2,6-Difluoro-4-methoxyphenyl)malonic acidYield 88%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3M aq. NaOH (80 mL) was added to a solution of diethyl 2-(2,6-difluoro-4-methoxyphenyl)malonate, 6.30 g, 20.85 mmol) in Et2O (5 mL). The reaction mixture was heated at reflux until all the solid had dissolved. After cooling, the mixture was acidified with 3M aq. HCl and the product was extracted with EtOAc (2×100 ml). The combined organic layers were dried (MgSO4) and solvent was removed in vacuo to give the title compound as a tan coloured solid (4.50 g, 88%); mp 157° C. (dec); 1H NMR (270 MHz, DMSO-d6) 3.78 (3H, s, CH3), 4.72 (1H, s, CH), 6.70-6.79 (2H, m, ArH).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux until all the solid
  3. dissolutionhad dissolved
  4. temperatureAfter cooling
  5. extractionthe product was extracted with EtOAc (2×100 ml)
  6. dry with materialThe combined organic layers were dried (MgSO4) and solvent
  7. customwas removed in vacuo

Sources & evidence

ORD record
ord-a003f24fa99042258fd3f48a4d32d03a
Source dataset
uspto-grants-2014_09
Patent number
US08846737B2

Reaction notes

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