Sodium Hydroxide → HCID 68432333, compound

HRID 889256Notes

Reaction equation

HRID 889256 reaction equation
C([O:8][C:9](=[O:25])[C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C1C=CC=CC=1.[OH-].[Na+]>CO>[CH2:18]([O:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([F:16])[C:10]=1[C:9]([OH:25])=[O:8])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 68430928HCID 68430928, compound

Product 1

HCID 68432333HCID 68432333, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7.3 g (21.7 mmol) of 2-benzyloxy-6-fluorobenzoic acid benzyl ester in 75 mL of methanol is added 20 mL of 1.0N NaOH. The mixture is stirred at 50° C. for 24 h. Another 10 mL of 1.0N NaOH is added and the mixture is stirred at RT for 18 h. The solvent is removed under reduced pressure and water is added to the residue. The solution is washed with MTBE and the aqueous phase is acidified with 1N HCl. The mixture is extracted with ethyl acetate (2×) and the organic solution is dried over sodium sulfate. The solvent is removed under reduced pressure to give the product as an oil: 1H NMR (CDCl3) δ 7.44-7.31 (m, 6H), 6.84-6.79 (m, 2H), 5.22 (s, 2H).

Workup

  1. stirringthe mixture is stirred at RT for 18 h
  2. customThe solvent is removed under reduced pressure and water
  3. additionis added to the residue
  4. washThe solution is washed with MTBE
  5. extractionThe mixture is extracted with ethyl acetate (2×)
  6. dry with materialthe organic solution is dried over sodium sulfate
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-80b0b966991540b6bd4abf02a271a994
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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