Hydrochloric Acid → 4-Fluoro-2-methylcinnamic acid

HRID 717095

Reaction equation

HRID 717095 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([CH3:10])[CH:3]=1.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1.Cl>N1C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:12]/[C:13]([OH:15])=[O:14])=[C:4]([CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 27832174-Fluoro-2-methylbenzaldehyde

Product 1

HCID 547757764-Fluoro-2-methylcinnamic acidYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

A stirred solution of 4-fluoro-2-methyl-benzaldehyde (20 g, 144.9 mmol) and malonic acid (30.1 g, 289.8 mmol) in pyridine (100 mL) was heated to 50° C. Piperidine (10 mL) was added and the reaction mixture was heated at 70° C. for 18 h. The reaction mixture was cooled RT and poured into chilled aqueous 1N HCl solution (1500 mL), the resulting precipitate was filtered and washed with petroleum ether 60-80 and dried in vacuo to obtain (E)-3-(4-fluoro-2-methylphenyl)acrylic acid (18 g, 69%) as an off white solid.

Workup

  1. temperatureThe reaction mixture was cooled RT
  2. additionpoured
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with petroleum ether 60-80
  5. customdried in vacuo

Sources & evidence

ORD record
ord-8f856b60844c4a909a0cce1f822c5b95
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Linked notes

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