3-(4-(Trifluoromethyl)phenyl)propan-1-ol → 3-[4-(Trifluoromethyl)phenyl]propanal

HRID 1929622Notes

Reaction equation

HRID 1929622 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][C:13]([F:25])([F:24])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][OH:23])=[CH:16][CH:15]=1>C(Cl)Cl>[F:12][C:13]([F:24])([F:25])[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][CH:22]=[O:23])=[CH:18][CH:19]=1

Participants

4

Reactant 2

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

Product 1

HCID 216838073-[4-(Trifluoromethyl)phenyl]propanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled orange suspension of pyridinium chlorochromate (3.659 g; 16.896 mmol) in anhydrous DCM (20 ml) was added dropwise a solution of 3-(4-trifluoromethyl-phenyl)-propan-1-ol (2.300 g; 11.264 mmol) in anhydrous DCM (35 ml). The resulting black suspension was allowed to warm-up to rt and was stirred under nitrogen for 3 h. The reaction mixture was directly filtered over silicagel using DCM. After concentration to dryness under reduced pressure, the product 3-(4-trifluoromethyl-phenyl)-propionaldehyde was isolated as a pale yellow oil (1.970 g; 86.5%). LC-MS: tR=0.95 min.; [M+H]+: no ionisation.

Workup

  1. filtrationThe reaction mixture was directly filtered over silicagel
  2. concentrationAfter concentration to dryness under reduced pressure

Sources & evidence

ORD record
ord-5a230912feb04f9eb494536f1bf862fe
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

Loading…