ChemicalBook CAS DataBase List 3-(3-(Trifluoromethyl)phenyl)propanal

3-(3-(Trifluoromethyl)phenyl)propanal synthesis

9synthesis methods

Product Name:3-(3-(Trifluoromethyl)phenyl)propanal
CAS Number:21172-41-8
Molecular formula:C10H9F3O
Molecular Weight:202.17

A solution of 3-(Trifluoromethyl) benzene propanol (1.0 g, 4.90 mmol) in dichloromethane (20 ml) is cooled in a water/ice bath, treated in succession with DMSO (770 mg, 9.80 mmol) and P2O5 (1.39 g, 9.80 mmol) and left under stirring for 30 minutes, while temperature raises to 20°C. The reaction mixture is then cooled in water/ice bath and triethylamine (2.4 ml, 17.15 mmol). The resulting solution is kept under stirring while the temperature raises to 20°C. After one hour, the mixture is treated with 5 per cent HCl, the phases are separated, and the organic one is further washed with 5 per cent HCl. The organic phase is then washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford 0.99 g of the aldehyde of 3-(3-(Trifluoromethyl)phenyl)propanal in quantitative yield.

78573-45-2 Synthesis

3-(3-(Trifluoromethyl)phenyl)propan-1-ol

78573-45-2
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21172-41-8
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Yield:21172-41-8 100%

Reaction Conditions:

Stage #1: 3-[3-(trifluoromethyl)phenyl]propan-1-olwith diphosphorus pentoxide;(methylsulfinyl)methane in dichloromethane at 20;Cooling with ice;Swern Oxidation;
Stage #2: with triethylamine in dichloromethane at 20;Cooling with ice;

Steps:

2

Example 2: Synthesis of 3-[3-(trifluoromethyl)phenyl]-propionaldehyde (II) A solution of compound (V) (1.0 g, 4.90 mmol) in dichloromethane (20 ml) is cooled in water / ice bath, treated in succession with DMSO (770 mg, 9.80 mmol) and P₂O₅ (1.39 g, 9.80 mmol) and left under stirring for 30 minutes, while temperature raises to 20°C. The reaction mixture is then cooled in water / ice bath and triethylamine (2.4 ml, 17.15 mmol). The resulting solution is kept under stirring while temperature raises to 20°C. After one hour the mixture is treated with 5% HCl, the phases are separated and the organic one is further washed with 5% HCl. The organic phase is then washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure, to afford 0.99 g of the aldehyde of formula (II) in quantitative yield. ¹H NMR (300 MHz, CDCl₃), ppm: 9.83 (t, 1H, J 0.9 Hz), 7.48-7.38 (m, 4H), 3.02 (t, 2H, J 7.2 Hz), 2.82 (m, 2H).

References:

EP2327684,2011,A1 Location in patent:Page/Page column 6

585-50-2 Synthesis