3-Cyclohexyl-2-dimethoxymethylacrylonitrile → 2-Cyano-3-cyclohexylpropenal

HRID 496822Notes

Reaction equation

HRID 496822 reaction equation
C[O:2][CH:3](OC)[C:4](=[CH:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:5]#[N:6]>Cl>[C:5]([C:4](=[CH:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[CH:3]=[O:2])#[N:6]

Participants

3

Reactant 1

HCID 543234033-Cyclohexyl-2-dimethoxymethylacrylonitrile

Product 1

HCID 571816332-Cyano-3-cyclohexylpropenalYield 76%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-(Dimethoxymethyl)-3-cyclohexylacrylonitrile, obtained from Example 3 (4.18 g, 0.02 mol) and 6N HCl (50 mL) were stirred together overnight at room temperature. The product was extracted with ethyl acetate (200 mL), the extract was dried) (MgSO4) and the ethyl acetate was evaporated in vacuo to give a 2.5 g (76%) of a brown oil which was used directly. A sample was distilled in a kugelrohr apparatus to give a pale yellow oil from which an analytical 2,4-dinitrophenyl hydrazone derivative was obtained as orange needles, mp 228-30° C.

Workup

  1. extractionThe product was extracted with ethyl acetate (200 mL)
  2. dry with materialthe extract was dried) (MgSO4)
  3. customthe ethyl acetate was evaporated in vacuo

Sources & evidence

ORD record
ord-4453313c10f14955a4e9e33705d4043f
Source dataset
uspto-grants-2005_09
Patent number
US06946554B2

Reaction notes

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