Sodium Hydroxide → 2,2-diethyl-3,4-dihydro-4-oxo-2H-1-benzopyran-6-carbonitrile

HRID 1460621Notes

Reaction equation

HRID 1460621 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8])(=[O:3])[CH3:2].[OH-].[Na+]>C1(C)C=CC=CC=1.C(C(CC)=O)C.N1CCCC1>[CH2:1]([C:4]1([CH2:11][CH3:10])[CH2:2][C:1](=[O:3])[C:4]2[CH:5]=[C:6]([C:7]#[N:8])[CH:9]=[CH:10][C:11]=2[O:12]1)[CH3:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 123328323-Acetyl-4-hydroxybenzonitrile

Product 1

HCID 143013512,2-diethyl-3,4-dihydro-4-oxo-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 7288Ethyl ketoneSolventHCID 31268PyrrolidineSolvent

Procedure

A solution of 16,1 g of 3-acetyl-4-hydroxybenzonitrile in 200 ml of toluene, 21 ml of diethylketone and 10 ml of pyrrolidin is refluxed for 31/2 hours in a Dean-Stark apparatus. The reaction solution cooled to room temperature is made alkaline with a 2N aq. sodium hydroxide solution and extracted with dichloroethane. The combined organic phases are washed with sodium hydroxidesolution and water, dried over sodiumsulfate and concentrated. The obtained residue is chromatographed on silica gel/dichloromethane. Recristallisation of the eluate from ether/hexane yields 2,2-diethyl-3,4-dihydro-4-oxo-2H-1-benzopyran-6-carbonitrile having a m.p. of 71°-72° C.

Workup

  1. extractionextracted with dichloroethane
  2. washThe combined organic phases are washed with sodium hydroxidesolution and water
  3. dry with materialdried over sodiumsulfate
  4. concentrationconcentrated
  5. customThe obtained residue is chromatographed on silica gel/dichloromethane

Sources & evidence

ORD record
ord-2f6c70168d89463d81990dcd3cb5379d
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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