Hydrochloric Acid → [2,3-Dichloro-4-(6-ethyl-3-(hydroxyimino)-1-cyclohexen-1-yl)phenoxy]acetic acid

HRID 1732180Notes

Reaction equation

[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14]2[CH:19]([CH2:20][CH3:21])[CH2:18][CH2:17][C:16](=O)[CH:15]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].Cl.[NH2:24][OH:25].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([C:14]2[CH:19]([CH2:20][CH3:21])[CH2:18][CH2:17][C:16](=[N:24][OH:25])[CH:15]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of [2,3-dichloro-4-(6-ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid (3.4 g, 0.01 mole), hydroxylamine hydrochloride (2.1 g, 0.03 mole) and pyridine (40 ml) were heated at 95° C. for 40 hours, poured into ice-water and hydrochloric acid, extracted with ether, washed with water, dried over magnesium sulfate and evaporated in vacuo. After recrystallization from toluene (120 ml) the [2,3-dichloro-4-(6-ethyl-3-(hydroxyimino)-1-cyclohexen-1-yl)-phenoxy]acetic acid hemitoluene solvate melted at 88°-90° C.

Workup

extractionextracted with ether
washwashed with water
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customAfter recrystallization from toluene (120 ml) the [2,3-dichloro-4-(6-ethyl-3-(hydroxyimino)-1-cyclohexen-1-yl)-phenoxy]acetic acid hemitoluene solvate melted at 88°-90° C.

Sources & evidence

ORD record: ord-ccee5fb2c3264971a32276a50299a727
Source dataset: uspto-grants-1986_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04625047

Reaction notes

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