Benzenebutanol → 4-Phenylbutanal

HRID 1991481Notes

Reaction equation

HRID 1991481 reaction equation
C[N+]1([O-])CCOCC1.[C:9]1([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[C:9]1([CH2:15][CH2:16][CH2:17][CH:18]=[O:19])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 76889BenzenebutanolHCID 82029Methyl morpholine oxide

Product 1

HCID 290304-PhenylbutanalYield 13%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tetrapropylammonium perruthenate(VII) (117 mg, 0.33 mmol, 0.1 equiv.) was added to a solution of 4 methylmorpholine N-oxide (580 mg, 5.00 mmol, 1.5 equiv.) and 4-phenyl-1-butanol (500 mg, 3.33 mmol, 1.0 equiv.) in acetonitrile (30 mL). The reaction mixture was stirred for 16 hours at room temperature then filtered through celite® then through a pad of silica (5 g) which was washed with acetonitrile (20 ml). The solvent was evaporated and the crude product purified by flash column chromatography (SiO2, ethyl acetate:heptane 5% to 50%) to afford crude 4-phenyl-1-butanal as a colourless oil, 62 mg (13% yield).

Workup

  1. filtrationthen filtered through celite®
  2. washthrough a pad of silica (5 g) which was washed with acetonitrile (20 ml)
  3. customThe solvent was evaporated
  4. customthe crude product purified by flash column chromatography (SiO2, ethyl acetate:heptane 5% to 50%)

Sources & evidence

ORD record
ord-2573072cf0784685a4d8f2be14a8c4a1
Source dataset
uspto-grants-2010_01
Patent number
US07645785B2

Reaction notes

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