Acetic Acid → 3,5-Di-tert-butylsalicylaldehyde

HRID 1110157Notes

Reaction equation

HRID 1110157 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[C:16](O)(=[O:18])C>>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:16]=[O:18])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 73112,4-Di-tert-butylphenol

Product 1

HCID 6880233,5-Di-tert-butylsalicylaldehyde

Procedure

It has now been found that reaction of 2,4-di-tert-butylphenol with hexamethylenetetramine in glacial acetic acid followed by quenching with water or aqueous acid, extraction with a water insoluble non-polar solvent and filtration through silica gel provides 3,5-di-tert-butylsalicylaldehyde in more than 60% yield and of a purity suitable for the production of chiral Mn-Salen catalysts. Alternatively, reaction of 2,4-di-tert-butylphenol with HMT in glacial acetic acid followed by quenching with an aqueous acid, separating the aqueous phase from the organic phase and recrystallizing the organic phase in methanol provides 3,5-di-tert-butylsalicylaldehyde in more than 40% isolated yield and a purity suitable (>95%) for the production of the catalyst.

Workup

  1. customby quenching with an aqueous acid
  2. customseparating the aqueous phase from the organic phase
  3. customrecrystallizing the organic phase in methanol

Sources & evidence

ORD record
ord-d254a8bbea184bb5818065182734c313
Source dataset
uspto-grants-1994_06
Patent number
US05324860

Reaction notes

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