Hydroxylamine HCl → 2,2,2-Trifluoro-1-(4-phenoxyphenyl)-ethanone oxime

HRID 1636023Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)=O.[Cl-].[OH:21][NH3+:22].C([O-])(=O)C.[Na+]>C(O)C.O>[F:1][C:2]([F:19])([F:18])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)=[N:22][OH:21]

Participants

Conditions

Temperature: 80 °C

Procedure

122 g (0.46 mol) of 2,2,2-trifluoro-1-(4-phenoxyphenyl)-ethanone are dissolved in 370 ml of ethanol and heated at 80° C. To the solution are added 33.3 g (0.48 mol) of hydroxylammonium chloride and 63.7 g (0.78 mol) of sodium acetate dissolved in 190 ml of water. The reaction mixture is refluxed for 5.5 hours, and poured into water. A pale yellow solid is precipitated. The solid is isolated by filtration and rinsed with water, and added in hexane and heated at 60° C. for 20 min. After cooling, the solid is isolated and rinsed with hexane, yielding 109 g of 2,2,2-trifluoro-1-(4-phenoxyphenyl)-ethanone oxime as a white solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 7.00-7.10 (m, 4H), 7.18 (t, 1H), 7.39 (t, 2H), 7.55 (d, 2H), 9.35 (br s, 1H).

Workup

temperatureThe reaction mixture is refluxed for 5.5 hours
customA pale yellow solid is precipitated
customThe solid is isolated by filtration
washrinsed with water
additionadded in hexane
temperatureheated at 60° C. for 20 min
temperatureAfter cooling
customthe solid is isolated
washrinsed with hexane

Sources & evidence

ORD record: ord-4cc458061f0f42f2b8b9feb76650fa3b
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06512020B1

Reaction notes

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