Benzenebutanol → 4-Phenylbutanal

HRID 1166079Notes

Reaction equation

HRID 1166079 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 76889BenzenebutanolHCID 159087Triacetoxyperiodinane

Product 1

HCID 290304-Phenylbutanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Phenylbutanol (700 mg, 4.66 mmol) was added to a solution of the Dess-Martin reagent (2.40 g, 5.66 mol) in dichloromethane (35 mL). After 30 min at RT, the solution was quenched with 10% aq. Na2S2O3, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), and concentrated. Purification by chromatography (SiO2, 9:1 hexane/ethyl acetate) yielded the title compound. MS 149 (M+H)+.

Workup

  1. customthe solution was quenched with 10% aq. Na2S2O3
  2. washwashed with sat. aq. NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, 9:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9195c46296a742a582865838144e7314
Source dataset
uspto-grants-2003_09
Patent number
US06613747B2

Reaction notes

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