Ethylene Glycol → HCID 54000011, compound

HRID 1387343Notes

Reaction equation

[CH2:1]([OH:4])[CH2:2]O.C1C=CC=CC=1.[CH3:11][C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=1)[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[N:26][O:27][CH3:28])[C:24]#[N:25].NCCO>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.C(OCC)(=O)C>[CH3:28][O:27][N:26]=[C:23]([C:24]1[O:4][CH2:1][CH2:2][N:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:14]1[CH:29]=[CH:30][CH:31]=[C:12]([CH3:11])[CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethylene glycol (2 ml) and benzene (10 ml) were added to 2-(3-methylphenoxymethyl)-α-methoxyiminophenyl-acetonitrile (1.0 g, 3.6 mmol), 2-aminoethanol (400 mg, 6.6 mmol) and zinc acetate dihydrate (100 mg, 0.46 mmol), and the mixture was subjected to azeotropic dehydration and stirred at 100° C. for 20 hours. After allowing the mixture to stand for cooling, ethyl acetate was added to the reaction mixture. The mixture was washed successively with water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetatein-hexane) to give 2-(3-methylphenoxymethyl)phenyl 2-oxazolin-2-yl ketone O-methyloxime (280 mg,24%) as an oil.

Workup

temperaturefor cooling
washThe mixture was washed successively with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel (ethyl acetatein-hexane)

Sources & evidence

ORD record: ord-e88177dce36742a5bb6a41f43db8cbe5
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268312B1

Reaction notes

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