Benzenebutanol → 4-Phenylbutanal

HRID 1889696Notes

Reaction equation

HRID 1889696 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>C(Cl)Cl>[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-PhenylbutanalYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-phenylbutan-1-ol (1.0 g, 6.6 mmol, 1.0 g) in DCM, cooled to 0° C. was added Dess Martin periodinane (8.4 g, 19.9 mmol, 3.0 eq). The reaction mixture was stirred at ambient temperature for 2 h, before being diluted with DCM and washed with 10% aq. NaHCO3 solution. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the desired product (600 mg, 61%); 1H NMR (400 MHz, CDCl3) δ 9.77-9.76 (s, 1H), 7.32-7.27 (m, 2H), 7.23-7.18 (m, 3H), 2.69-2.65 (t, 2H), 2.45-2.49 (t, 2H), 1.94-2.00 (m, 3H). MS (ESI): 166.2 (M+H)+.

Workup

  1. washwashed with 10% aq. NaHCO3 solution
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-530969689aa94469bb1d1a1358d88b66
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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