HCID 21559725, compound → HCID 68147443, compound

HRID 1578607Notes

Reaction equation

HRID 1578607 reaction equation
[CH:1]([CH2:3][C:4]([O:6]C(=O)CC=O)=[O:5])=O.[OH:12][C:13]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:14]=1[C:15]([CH2:17][C:18]#[N:19])=[O:16]>N1C=CC=CC=1>[C:4]([OH:6])(=[O:5])[CH3:3].[OH:24][C:22]1[CH:21]=[CH:20][C:14]2[C:15](=[O:16])[C:17]([C:18]#[N:19])=[CH:1][O:12][C:13]=2[CH:23]=1

Participants

4

Reactant 2

HCID 21559725HCID 21559725, compoundHCID 53941097HCID 53941097, compound

Product 1

HCID 68147443HCID 68147443, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

To a mixture of 105 g (1.2 mol) of formyl acetic anhydride and 40 ml of pyridine cooled to -10°C was added 16.5 g (0.1 mol) of 2,4-dihydroxybenzoylacetonitrile. This mixture was stirred overnight, allowing the reaction to warm to room temperature. The mixture was evaporated in vacuo and the residue was triturated with ethanol and filtered to give 23.3 g of crude material. Recrystallization of this solid from absolute ethanol gave 5.3 g of 7-hydroxy-4-oxo-4H-1-benzopyran-3 -carbonitrile acetate, mp 178°-180°C.

Workup

  1. customthe reaction
  2. temperatureto warm to room temperature
  3. customThe mixture was evaporated in vacuo
  4. customthe residue was triturated with ethanol
  5. filtrationfiltered
  6. customto give 23.3 g of crude material
  7. customRecrystallization of this solid from absolute ethanol

Sources & evidence

ORD record
ord-f79d4e1cfe784d8ea8bfe33136d7cba8
Source dataset
uspto-grants-1976_02
Patent number
US03937837

Reaction notes

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