Toluene → 2-Methoxymethyl-2-methyl-6-cyano-4-chromanone

HRID 654146Notes

Reaction equation

HRID 654146 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][O:14][CH2:15][C:16](=O)[CH3:17].N1CCCC1.C1(C)C=CC=CC=1>O>[CH3:13][O:14][CH2:15][C:16]1([CH3:17])[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 1140TolueneHCID 22172MethoxyacetoneHCID 31268PyrrolidineHCID 123328323-Acetyl-4-hydroxybenzonitrile

Product 1

HCID 150564792-Methoxymethyl-2-methyl-6-cyano-4-chromanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

a mixture of 50 g of 3-acetyl-4-hydroxybenzonitrile, 70 ml of methoxy-2-propanone, 6 ml of pyrrolidine and 300 ml of toluene is boiled in a water separator for 3 hours. The mixture is evaporated, the residue is worked up in the customary manner (ethyl acetate/dil. hydrochloric acid) and 2-methoxymethyl-2-methyl-6-cyano-4-chromanone is obtained, m.p. 79°-81° C.

Workup

  1. customThe mixture is evaporated

Sources & evidence

ORD record
ord-9562ccf88c7f43e1bc049adc16efce4c
Source dataset
uspto-grants-1992_07
Patent number
US05130322

Reaction notes

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