Acetic Acid → HCID 54134446, compound

HRID 866049Notes

Reaction equation

HRID 866049 reaction equation
[C:1]1([CH2:17]P(=O)(OCC)OCC)[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=1.C[O-].[Na+].C(O)(=O)C>CN(C)C=O.O>[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[CH:17][C:1]2[C:14]3[C:15]4=[C:16]5[C:11](=[CH:12][CH:13]=3)[CH:10]=[CH:9][CH:8]=[C:7]5[CH:6]=[CH:5][C:4]4=[CH:3][CH:2]=2)=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 1717536HCID 1717536, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 54134446HCID 54134446, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.47 g (7 mmol) of diethyl 1-pyrenylmethylphosphonate and 0.99 g (7 mmol) of 4-chlorobenzaldehyde were dissolved with stirring in 25 ml of N,N-dimethylformamide. To this reaction mixture, 1.62 g (7×1.2 mmol) of sodium methylate (28 wt. % methanol solution of sodium methylate) was gradually added in such a manner that the temperature of the reaction mixture did not exceed 30° C. The reaction mixture was then stirred at room temperature for 1 hour, neutralized with acetic acid, and diluted with about 300 ml of water. Crystals separated out. The crystals were separated by filtration, washed with water, dried and then purified by column chromatography two times. In the first time, the purification was carried out on a column of silica gel, using a mixed solvent of toluene/n-hexane (1/1) as the developing solvent, and in the second time, the purification was carried out on a column of silica gel, using a mixed solvent of toluene/n-hexane (1/2) as the developing solvent, whereby yellow 1-(4-chlorostyryl)pyrene was obtained with a yield of 2.21 g (93.5%).

Workup

  1. customdid not exceed 30° C
  2. customCrystals separated out
  3. customThe crystals were separated by filtration
  4. washwashed with water
  5. customdried
  6. custompurified by column chromatography two times
  7. customIn the first time, the purification
  8. customin the second time, the purification

Sources & evidence

ORD record
ord-13e2dd047881416f81072fd612cf70f4
Source dataset
uspto-grants-1996_10
Patent number
US05569800

Reaction notes

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