Trifluoroacetic acid → Benzaldehyde

HRID 1639600Notes

Reaction equation

HRID 1639600 reaction equation
FC(F)(F)[C:3]1[CH:9]=[CH:8][C:6](N)=[CH:5][CH:4]=1.F[C:13](F)(F)[C:14]([OH:16])=O>C(#N)C>[CH:5]1[CH2:6][CH:8]=[CH:9][CH:3]=1.[CH:14](=[O:16])[C:13]1[CH:8]=[CH:9][CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 99644-(Trifluoromethyl)aniline

Product 2

HCID 240BenzaldehydeYield 200%HCID 7612Cyclopentadiene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.84 g (30 mmol) of 4-trifluoromethylaniline are dissolved in 20 ml of acetonitrile, and 3.42 g (2.3 ml, 30 mmol) of trifluoroacetic acid are added (gives mixture A) 1.98 g (2.47 ml, 30 mmol) of freshly distilled cyclopentadiene and 3.18 g (3.05 ml, 30 mmol) of benzaldehyde are initially introduced with ice-cooling. Mixture A, pre-cooled to 5° C., is added to this solution, the mixture is allowed to come to room temperature and is stirred for 16 h. The mixture is then evaporated in vacuo. Purification by column chromatography gives the desired product.

Sources & evidence

ORD record
ord-cf26cf882ecb45949715cea0ef875527
Source dataset
uspto-grants-2012_02
Patent number
US08110583B2

Reaction notes

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