Acetone → 2,2-Dimethyl-4-oxo-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

HRID 273748Notes

Reaction equation

HRID 273748 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].[CH3:13][C:14]([CH3:16])=O.N1CCCC1.C1(C)C=CC=CC=1>O>[CH3:13][C:14]1([CH3:16])[CH2:2][C:1](=[O:3])[C:4]2[C:11](=[CH:10][CH:9]=[C:6]([C:7]#[N:8])[CH:5]=2)[O:12]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1140TolueneHCID 31268PyrrolidineHCID 123328323-Acetyl-4-hydroxybenzonitrile

Product 1

HCID 109545982,2-Dimethyl-4-oxo-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 81 g of 3-acetyl-4-hydroxybenzonitrile, 48 ml of acetone, 11.8 ml of pyrrolidine and 300 ml of toluene is allowed to stand at 20° for 1 hour, then boiled for 2 hours in a water separator and cooled. After customary working up, 2,2-dimethyl-6-cyano-4-chromanone is obtained, m.p. 119°-120°.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-bedab2e0fc4243f087935487d1a27e38
Source dataset
uspto-grants-1995_02
Patent number
US05387587

Reaction notes

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