Methanol → Cinnamoylbenzene

HRID 2380412Notes

Reaction equation

HRID 2380412 reaction equation
[OH-].[K+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)N=1)(=[O:5])[CH3:4].[CH:13](=O)[C:14]1[CH:19]=[CH:18][C:17](OC)=[CH:16][CH:15]=1.[CH3:23]O>O>[C:14]1([CH:13]=[CH:4][C:3]([C:6]2[CH:23]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:5])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 14797Potassium Hydroxide2×HCID 312444-MethoxybenzaldehydeHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 7189CinnamoylbenzeneYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium hydroxide (18.2 g, 325 mmol) was dissolved in 100 mL of H2O, and 100 mL of methanol was added. 2-Acetyl-6-bromopyridine (65 g, 325 mmol) and (68 g, 650 mmol) of p-anisaldehyde were dissolved together in 400 mL of methanol, and the solution was poured into the KOH solution. Precipitation of product began within a few minutes, and the reaction was allowed to stand at room temperature overnight. The precipitate was collected, washed with isopropanol, and dried to yield 79 g (76%) of the product as a yellow solid, mp 100°-102° C. FDMS (m/e) 317 M. An aliquot was purified by column chromatography on Woelm Silica gel, elution with 100% dichloromethane. Anal. Calcd for C15H12BrNO2 : C, 56.63; H, 3.80; N, 4.40. Found: C, 56.66;H, 3.87; N, 4.41. The NMR and IR spectra were consistent with the assigned structure and the product was homogeneous by TLC.

Workup

  1. customPrecipitation of product
  2. waitbegan within a few minutes
  3. customThe precipitate was collected
  4. washwashed with isopropanol
  5. customdried

Sources & evidence

ORD record
ord-f645d310e1b045a09273645e21e03f7e
Source dataset
uspto-grants-1994_11
Patent number
US05367080

Reaction notes

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