Hydrochloric Acid → 3-(3-Fluoro-4-methoxyphenyl)prop-2-enoic acid

HRID 1105942Notes

Reaction equation

HRID 1105942 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1.Cl>N1C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[CH:13][C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 676963-Fluoro-p-anisaldehyde

Product 1

HCID 1018433-(3-Fluoro-4-methoxyphenyl)prop-2-enoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A mixture of 3-fluoro-anisaldehyde (1.5 g) and malonic acid (2.08 g) in 5 ml pyridine was warmed until clear solution was obtained. To this mixture piperidine (0.4 ml) was added and then the content of the flask was heated at 80° C. for one (1) hour. It was further refluxed for 3 hours. At the end of this period the mixture was poured into 50 ml of cold water. It was then acidified by adding 5 ml of concentrated hydrochloric acid. Upon addition of acid, the solid separated, which was filtered and washed with cold water. The material was dried. Yield=1.7 g. The crude material was crystallized from a mixture of tetrahydrofuran and water. m.p. 227°-230° C.

Workup

  1. temperaturewas warmed until clear solution
  2. customwas obtained
  3. temperatureIt was further refluxed for 3 hours
  4. additionUpon addition of acid
  5. customthe solid separated
  6. filtrationwhich was filtered
  7. washwashed with cold water
  8. customThe material was dried
  9. customThe crude material was crystallized from a mixture of tetrahydrofuran and water

Sources & evidence

ORD record
ord-0f7e2957637846149951fe138d394917
Source dataset
uspto-grants-1982_01
Patent number
US04310675

Reaction notes

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