Benzenebutanol → 4-Phenylbutanal

HRID 966974Notes

Reaction equation

HRID 966974 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[C:23]1([CH2:29][CH2:30][CH2:31][CH2:32][OH:33])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[C:23]1([CH2:29][CH2:30][CH2:31][CH:32]=[O:33])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 76889BenzenebutanolHCID 159087Triacetoxyperiodinane

Product 1

HCID 290304-PhenylbutanalYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (1.7 g, 4.0 mmol) was added to a solution of benzenebutanol (0.5 g, 3.3 mmol) in dichloromethane (10 mL) and the mixture was stirred at room temperature for 2 hours. The mixture was filtered through a plug of silica gel, washing with dichloromethane, and the solvent was evaporated under reduced pressure to give the title compound as a colorless oil (466 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 9.76 (1H, m), 7.31-27 (2H, m), 7.22-7.16 (3H, m), 2.66 (2H, t, J 73 Hz), 2.45 (2H, t, J 7.3 Hz), 1.97 (2H, quin, J 7.3 Hz).

Workup

  1. filtrationThe mixture was filtered through a plug of silica gel
  2. washwashing with dichloromethane
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cab1a9fe7e6e48038163f35808bd11f6
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

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