Hydrochloric Acid → HCID 54090082, compound

HRID 1156841Notes

Reaction equation

HRID 1156841 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6](O)=O)[CH3:2].N1CCCCC1.C=O.Cl>O.N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:20])[C:5](=[CH2:6])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 53642612HCID 53642612, compound

Product 1

HCID 54090082HCID 54090082, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

66.45 g of 4-phenoxybutylmalonic acid ethyl ester, 45 ml of pyridine, 3 ml of piperidine and 9.9 g of paraformaldehyde are stirred together at 50° C. for 4 hours. After cooling, 400 ml of water are added to the reaction mixture which is then acidified with half-concentrated hydrochloric acid, while cooling with ice. The reaction mixture is then extracted 3 times with 200 ml of diethyl ether each time, the combined organic phases are concentrated and distilled in vacuo. 43.6 g 2-methylene-6-phenoxyhexanoic acid ethyl ester are obtained as a colorless liquid of b.p. 140° C. under 0.06 mm Hg (9 Pa).

Workup

  1. temperatureAfter cooling
  2. temperaturewhile cooling with ice
  3. extractionThe reaction mixture is then extracted 3 times with 200 ml of diethyl ether each time
  4. concentrationthe combined organic phases are concentrated
  5. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-67c10461db764d29978c1b92217ebf75
Source dataset
uspto-grants-1982_06
Patent number
US04337267

Reaction notes

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