Benzaldehyde → HCID 12857976, compound

HRID 1736388Notes

Reaction equation

HRID 1736388 reaction equation
N1C2C(=CC=CC=2)C=CC=1.[CH3:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.[CH:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)(=O)C1C=CC=CC=1>>[OH:29][CH:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 7047QuinolineHCID 70602-Methylquinoline

Product 1

HCID 12857976HCID 12857976, compoundYield 17.5%

Procedure

The method used is that of SKIDMORE and TIDD[The Quinoline series, Part I, 1641-1645, (1959)]. 5.3 ml of 2-methylquinoline (0.039 mol) and 3.56 ml of benzaldehyde 0.035 mol) are mixed with a little benzoic acid. The mixture is stirred at room temperature and the product is then left to crystallize for several weeks. The solution is filtered through sintered glass and the filter is rinsed with cold ethanol. The crystals remaining on the sintered glass are recrystallized in ethanol and then placed in a heating desiccator. 1.53 g of 2-(2-hydroxy-2-phenylethyl)quinoline are thereby obtained (Yld=24%). The filtrates are combined, the solvent is evaporated off therefrom and the products are then deposited on a silica column. 3.66 g of 2-methylquinoline and 1.9 g of 2-styrylquinoline are then obtained (Yld=18%). 69% of the starting 2-methylquinoline is recovered.

Workup

  1. waitthe product is then left
  2. customto crystallize for several weeks
  3. filtrationThe solution is filtered through sintered glass
  4. washthe filter is rinsed with cold ethanol
  5. customare recrystallized in ethanol
  6. customplaced in a heating desiccator

Sources & evidence

ORD record
ord-a7834f5805ca4d039b9e6079cf28ae8b
Source dataset
uspto-grants-1996_07
Patent number
US05541196

Reaction notes

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