Hydrochloric Acid → HCID 735856, compound

HRID 414290Notes

Reaction equation

HRID 414290 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1.Cl>O.N1C=CC=CC=1>[O:1]([C:8]1[CH:9]=[C:10](/[CH:11]=[CH:17]/[C:18]([OH:20])=[O:19])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic Acid2×HCID 8082PiperidineHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 735856HCID 735856, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-phenoxybenzaldehyde (214 g), malonic acid (300 g) and pyridine (450 cm3) was heated at 50° C. until all the malonic acid had dissolved, after which piperidine (20 cm3) was added and the mixture heated at 100° C. for 3 hours. The mixture was poured into iced water (3.0 l) and acidified with concentrated hydrochloric acid (600 cm3). The precipitated solid was collected by filtration, washed with water and then dissolved in chloroform. The chloroform solution was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulphate, after which the solvent was removed by evaporation under reduced pressure to give a solid residue which was recrystallised from a chloroform-hexane mixture to give E-3-(3-phenoxyphenyl)propenoic acid (219 g) as a white solid.

Workup

  1. dissolutionhad dissolved
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. dissolutiondissolved in chloroform
  5. washThe chloroform solution was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customafter which the solvent was removed by evaporation under reduced pressure
  8. customto give a solid residue which
  9. customwas recrystallised from a chloroform-hexane mixture

Sources & evidence

ORD record
ord-bd13fa2a69bd4a77babd16ad1150d233
Source dataset
uspto-grants-1988_12
Patent number
US04791139

Reaction notes

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