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

HRID 429929Notes

Reaction equation

HRID 429929 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>>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[OH:14])[C:8]([O:10][CH3:15])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

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

Product 1

HCID 13207060Methyl 3-tert-butyl-4-hydroxybenzoate

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 5h. 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-bydroxybenzoate 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 5h
  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
  10. customto afford 9.65 g (90%) of methyl 3-tert-butyl-4-bydroxybenzoate as a white crystalline solid, m.p. 144-145° C.

Sources & evidence

ORD record
ord-e2cdb6db4701492d8d25f17ab91a6f75
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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