Ammonium Hydroxide → 6-phenoxy-2H-1-benzopyran-3-carboxaldehyde

HRID 466190Notes

Reaction equation

HRID 466190 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH:14]=[CH:13][C:12]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:18](N1CCOCC1)=[O:19].P(Cl)(Cl)(Cl)=O.[OH-].[NH4+]>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][C:14]([CH:18]=[O:19])=[CH:13][C:12]=2[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 20417N-FormylmorpholineHCID 24813Phosphorus oxychlorideHCID 198156156-phenoxy-2H-1-benzopyran

Product 1

HCID 149712656-phenoxy-2H-1-benzopyran-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

6-Phenoxy-2H-1-benzopyran (3.36 g, 15 mmol) and N-formylmorpholine (10.4 g, 90 mmol) are dissolved in 10.5 ml of methylene chloride and treated with phosphorus oxychloride (13.8 g, 90 mmol) at 0° C. over 15 minutes. The mixture is then heated at 60° C. for 27 hours, cooled and poured slowly into an ice-water mixture. The mixture is then neutralized with aqueous ammonium hydroxide, and extracted twice with methylene chloride. The combined organic extracts are washed with water, dried (MgSO4), and evaporated to give crude 6-phenoxy-2H-1-benzopyran-3-carboxaldehyde, which is used without further purification.

Workup

  1. temperaturecooled
  2. extractionextracted twice with methylene chloride
  3. washThe combined organic extracts are washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-d06081969dae465aaa28a5bee1c87b47
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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