4-Nitrobenzaldehyde → 1-(4-nitrophenyl)-2-pyridin-2-ylethanol

HRID 280082Notes

Reaction equation

HRID 280082 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18].O>CO.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]([CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)[OH:9])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 962WaterHCID 79752-Methylpyridine

Product 1

HCID 3155881-(4-nitrophenyl)-2-pyridin-2-ylethanolYield 79%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A stainless steel bomb containing p-nitrobenzaldehyde (300 g, 1.99 moles), α-picoline (650 ml, 6.59 moles) and distilled water (100 ml, 5.56 moles) was sealed and held in an oil bath at 140°-160° C. for 19 hours. It was cooled to room temperature and opened to the atmosphere. The contents of the reactor, a mass of crystals and some dark liquid, were added to one liter of a 60:40 methanol-water mixture and the resulting mixture stirred for two hours. The solid was recovered by filtration, washed with one liter of the same solvent mixture and dried under vacuum at 50° C. to give 383-396 g (79%-82% yield) of ##STR29## 4-nitrophenyl-(α-picolyl)carbinol.

Workup

  1. customwas sealed
  2. filtrationThe solid was recovered by filtration
  3. washwashed with one liter of the same solvent mixture
  4. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-623ca4f2916440f89232635439f665ce
Source dataset
uspto-grants-1986_05
Patent number
US04588672

Reaction notes

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