4-[1,1-Dimethyl-3-(2-methoxyphenyl)-2-propynyloxy]benzonitrile → HCID 19895586, compound

HRID 1073966Notes

Reaction equation

HRID 1073966 reaction equation
[CH3:1][C:2]([CH3:22])([O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12]>ClC1C=CC=CC=1Cl>[CH3:12][O:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]1[C:21]2[CH:20]=[C:17]([C:18]#[N:19])[CH:16]=[CH:15][C:14]=2[O:13][C:2]([CH3:22])([CH3:1])[CH:3]=1

Participants

3

Reactant 1

HCID 198956454-[1,1-Dimethyl-3-(2-methoxyphenyl)-2-propynyloxy]benzonitrile

Product 1

HCID 19895586HCID 19895586, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

0.99 g of 4-[1,1-dimethyl-3-(2-methoxyphenyl)-2-propynyloxy]benzonitrile was dissolved in 10 ml of 1,2-dichlorobenzene and heated at reflux for 1.5 hours. After cooling the solution was evaporated and the residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. After recrystallization from petroleum ether (boiling point 60°-80° C.) there were obtained 480 mg of 4-(2-methoxyphenyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile of melting point 109°-111° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. temperatureAfter cooling the solution
  4. customwas evaporated
  5. customthe residue was chromatographed on silica gel
  6. washfor the elution
  7. customAfter recrystallization from petroleum ether (boiling point 60°-80° C.) there

Sources & evidence

ORD record
ord-4b11f7d6bccc4a2cb1e8bbaa02bb8e4d
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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