Ethanol → HCID 22036979, compound

HRID 1790003Notes

Reaction equation

HRID 1790003 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[O:12].[CH3:13][C:14]1C=CC(S(O)(=O)=O)=CC=1.[CH2:24]([OH:26])[CH3:25]>>[CH2:13]([O:12][CH:11]([O:26][CH2:24][CH3:25])[C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1)[CH3:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 796192-Quinolinecarboxaldehyde

Product 1

HCID 22036979HCID 22036979, compound

Procedure

A mixture of 2-quinolinecarboxaldehyde (0.08 mol) and 4-methylbenzenesulfonic acid (0.25 g) in ethanol (100 ml) was stirred and refluxed for 48 hours and brought to room temperature. The reaction was carried out again using the same quantities. The mixtures were combined. The solvent was evaporated. The residue was taken up in CH2Cl2. The organic solution was washed with K2CO3 10% and with H2O, then dried (MgSO4), filtered and the solvent was evaporated. The product was used without further purification, yielding 32.5 g of 2-(diethoxymethyl)quinoline (interm. 30).

Workup

  1. temperaturerefluxed for 48 hours
  2. custombrought to room temperature
  3. customThe solvent was evaporated
  4. washThe organic solution was washed with K2CO3 10% and with H2O
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe product was used without further purification

Sources & evidence

ORD record
ord-3d5a2eebd5444a19a9d7ea089a49bc03
Source dataset
uspto-grants-2006_07
Patent number
US07071192B1

Reaction notes

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