Ammonium fluoride → Methyl 5-hydroxy-2-methoxybenzoate

HRID 2230681Notes

Reaction equation

HRID 2230681 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([O:13][Si](C(C)(C)C)(C)C)=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[F-].[NH4+]>CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 25516Ammonium fluorideHCID 18464864Methyl 2-methoxy-5-(t-butyldimethylsilyloxy)benzoate

Product 1

HCID 592162Methyl 5-hydroxy-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine methyl 2-methoxy-5-(t-butyldimethylsilyloxy)benzoate (11.1 g. 37.4 mmol) and ammonium fluoride (6.94 g, 0.187 mmol) in methanol (150 mL). Heat to reflux. After 1 hour, evaporate in vacuo to give a residue. Partition the residue between ethyl acetate and water, separate the layers, extract the organic layer with water and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give methyl 2-methoxy-5-hydroxybenzoate: mp; 110-112° C. Rf=0.27 (silica gel, 5% ethyl acetate/hexane).

Workup

  1. temperatureHeat to reflux
  2. customevaporate in vacuo
  3. customto give a residue
  4. customPartition the residue between ethyl acetate and water
  5. customseparate the layers
  6. extractionextract the organic layer with water
  7. dry with materialDry the organic layer over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo

Sources & evidence

ORD record
ord-63e62a71704d4599919a1ae4aca0d587
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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