Pyridine → 1-(4-Bromophenyl)-2-p-tolylethane-1,2-dione

HRID 1284283Notes

Reaction equation

HRID 1284283 reaction equation
N1C=CC=CC=1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[OH:17])=[O:15])=[CH:10][CH:9]=1>O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)=[O:17])=[O:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 203722961-(4-Bromophenyl)-2-hydroxy-2-p-tolylethanone

Product 1

HCID 203722291-(4-Bromophenyl)-2-p-tolylethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cupric sulfate, 90 g. (0.36 mole), is stirred and heated on the steam-bath with 110 ml. of pyridine and 45 ml. of water until complete solution is obtained. 4-Bromo-4'-methylbenzoin, 55 g. (0.18 mole), is added and the mixture is stirred and heated on the steam-bath for 3 hours. During this period, the yellow crystalline product separates. After cooling and dilution with water, the product is collected, washed with water, 1 N hydrochloric acid, and water, and dried; m.p. 132°-135°C. The analytical sample is obtained as yellow needles, m.p. 136°-137°C, after repeated recrystallizations from 95% ethanol.

Workup

  1. temperatureheated on the steam-bath with 110 ml
  2. addition(0.18 mole), is added
  3. stirringthe mixture is stirred
  4. temperatureheated on the steam-bath for 3 hours
  5. waitDuring this period
  6. temperatureAfter cooling
  7. customdilution with water, the product is collected
  8. washwashed with water, 1 N hydrochloric acid, and water
  9. customdried
  10. customThe analytical sample is obtained as yellow needles, m.p. 136°-137°C
  11. customrecrystallizations from 95% ethanol

Sources & evidence

ORD record
ord-0b5b62d255774cf88d0eac6281e2275c
Source dataset
uspto-grants-1976_08
Patent number
US03978127

Reaction notes

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