3-Cyanocinnamyl alcohol → 3-Cyano-1-(2-formylethenyl)benzene

HRID 978678Notes

Reaction equation

HRID 978678 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH:6]=[CH:7][CH2:8][OH:9])#[N:2]>ClCCl.[O-2].[O-2].[Mn+4]>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH:6]=[CH:7][CH:8]=[O:9])#[N:2]

Participants

4

Reactant 1

HCID 537352473-Cyanocinnamyl alcohol

Product 1

HCID 544772143-Cyano-1-(2-formylethenyl)benzene

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of active manganese dioxide (20 g) in a solution of 3-cyanocinnamyl alcohol (Example 10(d), 4.0 g) in dichloromethane (100 ml) was stirred at room temperature for 16 hours. The mixture was filtered and the filtrate was evaporated to give the title product as a white solid, m.p. 100° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-36720285466347dca09b84ee119d3a42
Source dataset
uspto-grants-1987_05
Patent number
US04665189

Reaction notes

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