Methanol → Methyl 3-tert-butyl-4-hydroxybenzoate

HRID 369819Notes

Reaction equation

HRID 369819 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[OH:14])[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:15]O>>[CH3:15][O:9][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:13]([OH:14])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 144015103-tert-Butyl-4-hydroxybenzoic acid

Product 1

HCID 13207060Methyl 3-tert-butyl-4-hydroxybenzoateYield 90%

Procedure

To a 500 mL 3-necked flask equipped with a magnetic stirrer, a nitrogen inlet, and a condenser were added 10.0 g of 3-tert-butyl-4-hydroxybenzoic acid (ICN Biomedicals. Inc., Aurora, Ohio 44202), and 200 mL of MeOH. The solution was acidified by bubbling HCl gas through for 5 min. and was then heated at reflux for 5 h. The solution was cooled to RT and concentrated in vacuo to dryness. The resulting solid was dissolved in EtOAc. The solution was washed three times with 5% aqueous NaHCO3, dried over anhydrous MgSO4 and concentrated to dryness to afford 9.65 g (90%) of methyl-3-tert-butyl-4-hydroxybenzoate as a white crystalline solid, m.p. 144-145° C.

Workup

  1. customTo a 500 mL 3-necked flask equipped with a magnetic stirrer, a nitrogen inlet, and a condenser
  2. customby bubbling HCl gas through for 5 min.
  3. temperaturewas then heated
  4. temperatureat reflux for 5 h
  5. concentrationconcentrated in vacuo to dryness
  6. dissolutionThe resulting solid was dissolved in EtOAc
  7. washThe solution was washed three times with 5% aqueous NaHCO3
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5f18cf5508bb42788a6a943cf0dd4483
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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