Acetic Acid → HCID 348326, compound

HRID 1607405Notes

Reaction equation

HRID 1607405 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[CH:9]1[CH:14]=[C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]=O)[C:12]2=[CH:11][CH:10]=1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:8])[C:5]([C:6]#[N:7])=[CH:19][C:18]1[C:12]2[C:13](=[CH:14][CH:9]=[CH:10][CH:11]=2)[CH:15]=[CH:16][CH:17]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 61951-NaphthaldehydeHCID 7764Ethyl cyanoacetateHCID 8082Piperidine

Product 1

HCID 348326HCID 348326, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 7.8 g of cyanoacetic acid ethyl ester and 10.0 g of 1-naphthylaldehyde in 150 ml of benzene were added 2 ml of piperidine and 2 ml of acetic acid, the mixture was heated under reflux for 3 hours while removing water formed during the reaction using a molecular sieve. After cooling, the reaction mixture was washed successively with a saturated sodium bicarbonate aqueous solution, water, diluted hydrochloric acid and water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from benzene-hexane to obtain 13.8 g of 2-cyano-3-(1-naphthyl)propenoic acid ethyl ester as light yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customwhile removing water
  4. customformed during the reaction
  5. temperatureAfter cooling
  6. washthe reaction mixture was washed successively with a saturated sodium bicarbonate aqueous solution, water, diluted hydrochloric acid and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-6ee0e3830e7b443eb6ee8e7f4ac6b21b
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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