Lithium hydroxide, monohydrate → (RS)-(2,6-difluoro-3-hydroxy-phenyl)-methoxy-acetic acid

HRID 1247390Notes

Reaction equation

HRID 1247390 reaction equation
C([O:3][C:4](=[O:17])[CH:5]([C:8]1[C:13]([F:14])=[CH:12][CH:11]=[C:10]([OH:15])[C:9]=1[F:16])[O:6][CH3:7])C.O[Li].O>C1COCC1.CO.O>[F:16][C:9]1[C:10]([OH:15])=[CH:11][CH:12]=[C:13]([F:14])[C:8]=1[CH:5]([O:6][CH3:7])[C:4]([OH:17])=[O:3]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69290294(RS)-(2,6-difluoro-3-hydroxy-phenyl)-methoxy-acetic acid ethyl ester

Product 1

HCID 69290134(RS)-(2,6-difluoro-3-hydroxy-phenyl)-methoxy-acetic acidYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (RS)-(2,6-difluoro-3-hydroxy-phenyl)-methoxy-acetic acid ethyl ester (11.6 g) and LiOH.H2O in THF (40 ml), MeOH (40 ml) and H2O was stirred 2 h at 65° C. The organic solvents were evaporated, H2O was added (50 ml) and the pH was lowered with 2 N HCl to pH=2. The product was extracted with AcOEt (3×50 ml). The organic layers were washed with brine (100 ml), combined and dried (Na2SO4). Evaporation of the solvent afforded 9.6 g (94%) of (RS)-(2,6-difluoro-3-hydroxy-phenyl)-methoxy-acetic acid. White solid. MS 217.1 ([M−H]−).

Workup

  1. customThe organic solvents were evaporated
  2. additionH2O was added (50 ml)
  3. extractionThe product was extracted with AcOEt (3×50 ml)
  4. washThe organic layers were washed with brine (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-454b4263a33e43dcb412dbf5de644a70
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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