Formaldehyde → Ethyl 2-cyanopropionate

HRID 1076278Notes

Reaction equation

HRID 1076278 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[C:9]1(C=CC(O)=CC=1)O.N1CCCCC1.C=O>[Pd].O.C(O)(=O)C.C1(C)C=CC=CC=1>[C:1]([CH:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 785HydroquinoneHCID 7764Ethyl cyanoacetateHCID 8082Piperidine2×

Product 1

HCID 98018Ethyl 2-cyanopropionate

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Using the procedure of Example 9 with 3,616 parts of ethyl cyanoacetate, 10 parts of hydroquinone, 4.3 parts of piperidine, 45 parts of a 3% palladium on charcoal catalyst and 6,500 parts of toluene, treated over 4 hours with 4,000 parts of a solution of 3,000 parts of formalin (36%), 225 parts of glacial acetic acid, 258 parts of piperidine and water to give a total of 4,500 parts, gave 1,488 parts of crude ethyl 2 cyanopropionate which on redistillation yielded 1198.5 parts of a purified product of boiling point 83°-85°C/12-13 mm. of mercury.

Workup

  1. customto give a total of 4,500 parts

Sources & evidence

ORD record
ord-ed7b914f1ddd49369eeeeb9dfe16f97c
Source dataset
uspto-grants-1976_05
Patent number
US03956357

Reaction notes

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