Butanal → 3,5-Di-tert-butyl-2-[(butylamino)methyl]phenol

HRID 1173302

Reaction equation

HRID 1173302 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:9]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:8][C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:6][C:5]=1[OH:18].[CH:19](=O)[CH2:20][CH2:21][CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C.C(Cl)Cl>[C:10]([C:9]1[C:4]([CH2:3][NH:2][CH2:19][CH2:20][CH2:21][CH3:22])=[C:5]([OH:18])[CH:6]=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=1)([CH3:11])([CH3:12])[CH3:13]

Participants

7

Reactant 3

HCID 261ButanalHCID 5049666Sodium triacetoxyborohydrideHCID 452597712-(Aminomethyl)-3,5-di-tert-butylphenol hydrochloride

Product 1

HCID 104470183,5-Di-tert-butyl-2-[(butylamino)methyl]phenol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.47 g (2.0 mmol) of the product of Example 19 and 0.15 g (2.1 mmol) of n-butyraldehyde in 10 mL of 1,2-dichloroethane was added 25 drops of acetic acid and 3 g of finely powdered 4 Å molecular sieves. The mixture was stirred 5 h at room temperature at which point 1 g of sodium triacetoxyborohydride was added. The reaction mixture was stirred overnight at room temperature, then diluted with 10 mL CH2Cl2 and filtered through a layer of Celite filter aid. The filtrate was washed with excess saturated aq. NaHCO3, the aqueous layer was extracted with CH2Cl2, then the organic layers were combined, dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0-10% EtOAc in CH2Cl2. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. filtrationfiltered through a layer of Celite
  4. filtrationfilter aid
  5. washThe filtrate was washed with excess saturated aq. NaHCO3
  6. extractionthe aqueous layer was extracted with CH2Cl2
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified on a silica gel flash chromatography column
  11. washeluted with 0-10% EtOAc in CH2Cl2
  12. customEvaporation of the purified fractions
  13. customdrying in vacuo

Sources & evidence

ORD record
ord-48426b178a3b48afaefe2b0d4350c5e8
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Linked notes

Loading…