Hydrochloric Acid → 4-Chloro-3-fluorocinnamic acid

HRID 2365801Notes

Reaction equation

HRID 2365801 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1C=CC=CC=1.Cl>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:4][C:3]=1[F:10]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 1049PyridineHCID 27249854-Chloro-3-Fluorobenzaldehyde

Product 1

HCID 57084034-Chloro-3-fluorocinnamic acidYield 92.7%

Conditions

Temperature
50 °C

Procedure

4-Chloro-3-fluorobenzaldehyde (15.0 g, 94.6 mmol) was combined with malonic acid (10.8 g, 104 mmol) and pyridine (11.5 mL, 142 mmol). The mixture was heated to 50° C. and agitated 1 hour. Then it was heated to 100° C. and agitated 16 hours. Ice (100 g) and 6M HCl (25 mL) were added, and the mixture was agitated one hour. Precipitation was filtered, washed with water and dried in vacuo to give (E)-3-(4-chloro-3-fluorophenyl)acrylic acid (17.6 g, 87.7 mmol, 92.7% yield) as a solid.

Workup

  1. temperatureThen it was heated to 100° C.
  2. stirringagitated 16 hours
  3. stirringthe mixture was agitated one hour
  4. customPrecipitation
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-87a655ccc43f402a9578067e1e8d5ac0
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

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