Formaldehyde → HCID 10489014, compound

HRID 2285741Notes

Reaction equation

HRID 2285741 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6](O)=O)[CH3:2].C=O.N1C=CC=CC=1.N1CCCCC1>O>[CH2:1]([O:3][C:4](=[O:18])[C:5](=[CH2:6])[CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1049PyridineHCID 8082PiperidineHCID 10586761HCID 10586761, compound

Product 1

HCID 10489014HCID 10489014, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g of 3-phenylpropylmalonic acid monoethyl ester, 7.5 g of paraformaldehyde, 37.5 ml of pyridine and 2.5 ml of piperidine are stirred together at 50° C. for 5 hours. After cooling, 350 ml of water are added to the reaction mixture, and the mixture is then extracted 3 times with 150 ml of hexane each time. After washing with 1 N hydrochloric acid, water and sodium bicarbonate solution, the organic phase is concentrated and distilled. 5-Phenyl-2-methylenevaleric acid ethyl ester is obtained as a colorless liquid of b.p. 78° to 79° C. under 0.02 mm Hg.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture is then extracted 3 times with 150 ml of hexane each time
  3. washAfter washing with 1 N hydrochloric acid, water and sodium bicarbonate solution
  4. concentrationthe organic phase is concentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-92ba08e818934e11b2594778c89d0d27
Source dataset
uspto-grants-1982_04
Patent number
US04324796

Reaction notes

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