Potassium Hydroxide → Benzoic acid, 2-fluoro-3-(phenylmethoxy)-

HRID 2395386Notes

Reaction equation

HRID 2395386 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([F:25])=[C:11]([CH:22]=[CH:23][CH:24]=1)[C:12]([O:14]CC1C=CC=CC=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH2:1]([O:8][C:9]1[C:10]([F:25])=[C:11]([CH:22]=[CH:23][CH:24]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18971735HCID 18971735, compound

Product 1

HCID 18971725Benzoic acid, 2-fluoro-3-(phenylmethoxy)-Yield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl 3-benzyloxy-2-fluorobenzoate (7.13 g, 21 mmol) in methanol (40 ml) was added an aqueous solution of potassium hydroxide (2.38 g, 42 mmol in 40 ml of water) and the mixture heated at reflux for 30 min. The reaction mixture was cooled, washed with diethyl ether (20 ml) and the ethereal layer was discarded. The aqueous layer was acidified to pH 2 with concentrated HCl and extracted with ethyl acetate (3×40 ml). The combined organic extracts were washed with brine (20 ml), dried (MgSO4) and evaporated to afford title compound (4.83 g, 85%) as white solids.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 30 min
  3. temperatureThe reaction mixture was cooled
  4. washwashed with diethyl ether (20 ml)
  5. extractionextracted with ethyl acetate (3×40 ml)
  6. washThe combined organic extracts were washed with brine (20 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-03c54bf9f22e49ff8651197cf2f710f8
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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