Acetic Acid → 3-(4-Methoxyphenyl)prop-2-enal

HRID 895955

Reaction equation

HRID 895955 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][C:9]#N)=[CH:5][CH:4]=1.O.CC(O)=[O:16]>[Ni].N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][CH:9]=[O:16])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 342403-(4-Methoxyphenyl)prop-2-enenitrile

Product 1

HCID 2309953-(4-Methoxyphenyl)prop-2-enalYield 35%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To 2 g (12.6 mmol) 4-methoxycinnamonitrile in 10:10:20 ml H2O:HOAc:pyridine was added 5 g (47 mmol) NaH2PO2 (hypophosphite) followed by 2 g RaNi. After stirring 3 hours at 50° C., the reaction mixture was filtered, extracted with CH2Cl2, washed with dilute HCl, washed with H2O and evaporated to give 0.7 g (35% yield) 4-methoxycinnamaldehyde, a yellow solid, m.p. 47° C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. extractionextracted with CH2Cl2
  3. washwashed with dilute HCl
  4. washwashed with H2O
  5. customevaporated

Sources & evidence

ORD record
ord-69f1bb31c39f41839482b13f761928dd
Source dataset
uspto-grants-2005_07
Patent number
USRE038761E1

Linked notes

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