Acetic Acid → HCID 86739119, compound

HRID 1649400Notes

Reaction equation

HRID 1649400 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]([CH2:8][Cl:9])=[O:7])[CH3:2].C(=O)[C:12]1[O:16][CH:15]=[CH:14][CH:13]=1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1.CCOCC.O>[CH2:1]([O:3][C:4](=[O:10])[C:5](=[C:12]1[CH2:13][CH:14]=[CH:15][O:16]1)[C:6](=[O:7])[CH2:8][Cl:9])[CH3:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7362FurfuralHCID 8082PiperidineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 86739119HCID 86739119, compoundYield 86.8%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

200 g of 4-chloroacetoacetic acid ethyl ester, 125.6 g of freshly distilled furfural, 2.6 ml of piperidine and 7 ml of glacial acetic acid were dissolved in 120 ml of benzene and the solution was boiled for 5 hours, using a water separator. 1 liter of ether was added to the cooled solution and the mixture was then extracted in each case once by shaking with saturated sodium bicarbonate solution, water, 2 M citric acid solution and again with water. After the extract had been dried over magnesium sulphate and concentrated, an oil was obtained and was subjected to incipient distillation under a high vacuum. The product remained as a viscous oil and the E/Z isomer ratio was 4:1. Yield: 86.8%.

Workup

  1. extractionthe mixture was then extracted in each case once
  2. dry with materialAfter the extract had been dried over magnesium sulphate
  3. concentrationconcentrated
  4. customan oil was obtained
  5. distillationwas subjected to incipient distillation under a high vacuum

Sources & evidence

ORD record
ord-3c6f9d6df0c84854941e614c585f2f0f
Source dataset
uspto-grants-1983_11
Patent number
US04416880

Reaction notes

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