Methanol → Methyl 3,5-di-tert-butyl-4-hydroxybenzoate

HRID 866300Notes

Reaction equation

HRID 866300 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([OH:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH3:19]O>>[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8]([O:10][CH3:19])=[O:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acid

Product 1

HCID 75639Methyl 3,5-di-tert-butyl-4-hydroxybenzoate

Procedure

In a 500 cc 1-necked, round bottom flask, fitted with a condenser and stirring bar, were placed under nitrogen: 37.55 g. (0.15 mole) 3,5-di-tert.-butyl-4-hydroxybenzoic acid, 7.5 g. Amberlyst 15 catalyst, and 300 cc (7.43 moles) methanol. The solution was refluxed 15 hours, after which time the hot solution was filtered, concentrated, and cooled to afford 31.9 g. (81%) white crystals which were washed with hexane and dried. The melting point was 165.0° -166.5° C. The infrared and NMR spectra of the product were consistent with those expected from methyl 3,5-di-tert. butyl-4-hydroxybenzoate.

Workup

  1. customIn a 500 cc 1-necked, round bottom flask, fitted with a condenser
  2. temperatureThe solution was refluxed 15 hours
  3. filtrationafter which time the hot solution was filtered
  4. concentrationconcentrated
  5. temperaturecooled
  6. customto afford 31.9 g
  7. wash(81%) white crystals which were washed with hexane
  8. customdried

Sources & evidence

ORD record
ord-a0102870a7f34a29a769332285850358
Source dataset
uspto-grants-1978_07
Patent number
US04098709

Reaction notes

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