Acetic Acid → 3,5-Di-tert-butylsalicylaldehyde
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].C1N2CN3CN(C2)CN1C3.[C:26](O)(=[O:28])C>>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:26]=[O:28])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]Participants
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
- customby quenching with water or aqueous acid, extraction with a water insoluble non-polar solvent and filtration through silica gel
Sources & evidence
- ORD record
- ord-96407ec8d27940e89b86853fa5cb7477
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05324860
Reaction notes
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