Hydrochloric Acid → 3-[4-(Trifluoromethyl)phenyl]prop-2-enoic acid

HRID 1843892Notes

Reaction equation

[C:1](O)(=O)[CH2:2][C:3]([OH:5])=[O:4].[F:8][C:9]([F:19])([F:18])[C:10]1[CH:17]=[CH:16][C:13](C=O)=[CH:12][CH:11]=1.C(OC(=O)C)C.Cl>N1C=CC=CC=1.CCCCCC.N1CCCCC1>[F:8][C:9]([F:19])([F:18])[C:10]1[CH:17]=[CH:16][C:13]([CH:1]=[CH:2][C:3]([OH:5])=[O:4])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 105 °C

Procedure

Malonic acid (3.58 g, 0.03 mol) and piperidine (0.28 mL, 0.0028 mol) were added to a solution of 4-trifluoromethyl-benzaldehyde (5 g, 0.028 mol) in pyridine (50 mL) at room temperature under nitrogen atmosphere. The resulting mixture was refluxed at 105° C. for 20 minutes under nitrogen atmosphere. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was cooled to room temperature, followed by the addition of 6N HCl and filtered. The residue was washed with n-hexane (20 mL) and dried under reduced pressure to afford 7.2 g of the crude product which was used in the next step without further purification.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
washThe residue was washed with n-hexane (20 mL)
customdried under reduced pressure

Sources & evidence

ORD record: ord-ed0ac94ff4e4443bbf01eb3b97947c82
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946260B2

Reaction notes

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