HCID 13393783, compound → 2-Phenyl-2H-1-benzopyran-3-carbaldehyde

HRID 978779Notes

Reaction equation

HRID 978779 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[O:19].O.[SH-].[Na+]>C(O)C>[CH:18]([C:3]1[CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:5][C:6]2[C:11]([CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:19]

Participants

4

Reactant 2

HCID 13393783HCID 13393783, compoundHCID 16211346Sodium hydrosulfide hydrate

Product 1

HCID 30446102-Phenyl-2H-1-benzopyran-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 26 g 4-chloro-3-formyl-flav-3-ene and 7.1 g sodium hydrosulfide hydrate in 400 ml ethanol is refluxed for 3 hours and allowed to stand overnight at room temperature. The reaction mixture is evaporated to dryness and the residue dissolved in methylene chloride. The precipitate is filtered and the organic solution is evaporated. The residue is recrystallized in a mixture of hexane and toluene. Pure 4-(2"H-3"-formyl-2"-phenyl-1"-benzopyran-4"-yl-thio)-3-formyl-flav-3-ene is obtained as yellow crystals; m.p. 193°-194° C.

Workup

  1. temperatureis refluxed for 3 hours
  2. customThe reaction mixture is evaporated to dryness
  3. dissolutionthe residue dissolved in methylene chloride
  4. filtrationThe precipitate is filtered
  5. customthe organic solution is evaporated
  6. customThe residue is recrystallized in a mixture of hexane and toluene

Sources & evidence

ORD record
ord-3818d1da5e0146b4970d294815e072fd
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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