2-Phenylacetophenone → HCID 57170110, compound

HRID 2286526Notes

Reaction equation

HRID 2286526 reaction equation
[C:1]1([C:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16][N:17]([CH3:22])[N:18]=[CH:19][CH:20]=O.[O-]CC.[Na+].[Na]>C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:16][N:17]([CH3:22])[N:18]=[CH:19][CH:20]=[C:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:8]

Participants

7

Reactant 4

HCID 99482-Phenylacetophenone2×HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 54434754HCID 54434754, compound2×

Product 1

HCID 57170110HCID 57170110, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 21584019Toluene ethylacetateSolvent

Procedure

To a mixture of 19.6 g (0.1 mole) desoxybenzoin and 10 g (0.1 mole) of glyoxal mono(dimethylhydrazone) in 100 ml ethanol was added dropwise a solution of sodium ethoxide prepared by dissolving 2.3 g (0.1 mole) sodium metal in 100 ml ethanol. The mixture was heated at reflux for one-half hour. TLC (90/10, toluene/ethyl acetate) showed a small amount of starting desoxybenzoin, so 2.0 g (0.02 mole) of additional glyoxal mono(dimethylhydrazone) was added. Heating was continued another two hours. TLC at this time showed no starting material, and two clean close yellow product spots (isomers). The mixture was poured into 1 l ice water and then extracted with methylene chloride. The organic extracts were dried and concentrated on a rotary evaporator to give 28.7 g (100%) of yellow oil. The NMR showed the presence of two major N(CH3)2 containing materials (product isomers). The crude oil crystallized from isopropanol to give one pure isomer of product, 13.4 g (48%), pale yellow crystals, m.p. 131°-2°.

Workup

  1. customprepared
  2. temperatureThe mixture was heated
  3. temperatureat reflux for one-half hour
  4. additionwas added
  5. temperatureHeating
  6. extractionextracted with methylene chloride
  7. customThe organic extracts were dried
  8. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-9f1ac4e07d724f43b84575f26003c2c6
Source dataset
uspto-grants-1981_05
Patent number
US04267190

Reaction notes

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