Ammonium fluoride → Methyl 5-hydroxy-2-methoxybenzoate

HRID 637219Notes

Reaction equation

HRID 637219 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 uacuo 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 uacuo

Sources & evidence

ORD record
ord-cc63f7f2d2c947808406a91e56a6584e
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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