Malonic Acid → HCID 735855, compound

HRID 1164473Notes

Reaction equation

HRID 1164473 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3](O)=O.[O:8]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)C=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1CCCCC1>N1C=CC=CC=1>[O:8]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:3]=[CH:2][C:1]([OH:7])=[O:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 735855HCID 735855, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

62.4 g of malonic acid are dissolved in 100 ml of pyridine. After termination of the exothermal reaction, 99 g of 3-phenoxybenzaldehyde and 5 g of piperidine are added, the batch is refluxed for 3 hours, cooled to 25° C. and poured onto ice/concentrated hydrochloric acid in order to wash out pyridine and piperidine, while the acid precipitates in the form of crystals. After drying, 113.7 g (95% of theory) of 3-phenoxycinnamic acid, m.p. 107°-109° C., are obtained. 18 g (0.15 mol) of thionyl chloride are added to a suspension of 24 g (0.1 mol) of 3-phenoxycinnamic acid in 100 ml of toluene, and stirred for 3 hours at 30° C. After removal of the solvent in vacuo, distillation is carried out. 24.6 g (95% of theory) of 3-(2-phenoxyphenyl)-2-propenic acid chloride, b.p. 155°-158° C./0.2 mm Hg, are obtained.

Workup

  1. additionare added
  2. temperaturethe batch is refluxed for 3 hours
  3. additionpoured onto ice/concentrated hydrochloric acid in order
  4. washto wash out pyridine and piperidine, while the acid
  5. customprecipitates in the form of crystals
  6. customAfter drying

Sources & evidence

ORD record
ord-cec9aaa58e4f44b1aa32fda69d35ea8f
Source dataset
uspto-grants-1983_01
Patent number
US04370277

Reaction notes

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