4-Methylbenzaldehyde → HCID 54356080, compound

HRID 1709235Notes

Reaction equation

HRID 1709235 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH:1][C:2]2[N:11]=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([OH:6])=[O:5])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 14798Sodium HydroxideHCID 7015327Methyl 2-methylnicotinate

Product 1

HCID 54356080HCID 54356080, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture consisting of 15.1 g of methyl 2-methylnicotinate, 36.0 g of 4-methylbenzaldehyde and 15.0 g of anhydrous zinc chloride was stirred for 30 minutes at 180° C. The resulting reaction mixture was cooled to room temperature. Thereto were added 151 ml of a 10% aqueous sodium hydroxide solution and 100 ml of toluene. The resulting mixture was stirred. The insolubles were removed by filtration. An aqueous layer was separated, washed with toluene and then adjusted to pH 5.0 with acetic acid. The resulting crystals were collected by filtration and dried to obtain 13.2 g of 2-(p-methylstyryl)nicotinic acid. It was recrystallized from ethanol to obtain 10.6 g of colorless crystals having a melting point of 208°-209° C.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas cooled to room temperature
  3. stirringThe resulting mixture was stirred
  4. customThe insolubles were removed by filtration
  5. customAn aqueous layer was separated
  6. washwashed with toluene
  7. filtrationThe resulting crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-ded85972039642658edbc0e117b0f529
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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