Heptane → 3-[4-(Trifluoromethyl)phenyl]propanal

HRID 1172591Notes

Reaction equation

HRID 1172591 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.CCCCCCC>C(Cl)Cl>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8900HeptaneHCID 224436423-(4-(Trifluoromethyl)phenyl)propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 216838073-[4-(Trifluoromethyl)phenyl]propanalYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In an inert atmosphere, 3-(4-trifluoromethyl-phenyl)-propan-1-ol (1.02 g, 5 mmol) was dissolved in DCM (10 ml) and slowly added to a suspension of PCC (1.61 g, 7.5 mmol) in anhydrous DCM (15 ml). Stirring was continued for 4 h at rt. Anhydrous heptane (10 ml) was added to the reaction mixture followed by filtration over a pad of silicagel (15 g). The filtrate was evaporated to give 850 mg of 3-(4-trifluoromethyl-phenyl)-propionaldehyde. LC-MS: tR=0.94 min; [M+H]+=no ionisation.

Workup

  1. filtrationfollowed by filtration over a pad of silicagel (15 g)
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-8f98a2a992cb43d6be848dd74b135cc5
Source dataset
uspto-grants-2010_11
Patent number
US07834028B2

Reaction notes

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