Isopropanol → 3-(4-Bromo-3,5-dimethylphenyl)propanal

HRID 237534Notes

Reaction equation

HRID 237534 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][C:3]=1[CH3:13].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(O)(C)C>ClCCl>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:4][C:3]=1[CH3:13]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 159087Triacetoxyperiodinane2×HCID 866971963-(4-Bromo-3,5-dimethylphenyl)propan-1-ol

Product 1

HCID 866971973-(4-Bromo-3,5-dimethylphenyl)propanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 3-(4-bromo-3,5-dimethylphenyl)propan-1-ol (250 mg) in dichloromethane (5 mL) is added at 0° C. 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-on (Dess-Martin periodinan, 2.7 mL of a 15% solution in dichloromethane). The mixture is stirred for 12 hours at room temperature, cooled to 0° C. and 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-on (Dess-Martin periodinan, 1.6 mL of a 15% solution in dichloromethane) is added. After stirring for 4 hours isopropanol (5 mL) is added, the mixture is stirred for 15 minutes and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. Yield: 120 mg; LC (method 8): tR=0.38 min; Mass spectrum (ESI−): m/z=239 [M−H]−.

Workup

  1. temperaturecooled to 0° C.
  2. additionis added
  3. stirringthe mixture is stirred for 15 minutes
  4. customthe solvents are evaporated in vacuo
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30)

Sources & evidence

ORD record
ord-645b367875914a49aa2c5c2c752e7a88
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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