O-(4-Nitrophenyl)hydroxylamine → (2-Butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone

HRID 1897854Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10]N)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:27])[CH2:20][C:21](=O)[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][CH:14]=1>C(O)(=O)C>[CH2:22]([C:21]1[O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[C:20]=1[C:19](=[O:27])[C:16]1[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=1)[CH2:23][CH2:24][CH3:25]

Participants

Conditions

Temperature: 70 °C

Procedure

O-4-nitrophenylhydroxylamine (1.0 g), was suspended in acetic acid (10 ml) and 1-(4-hydroxyphenyl)-heptane-1,3-dione (1.36 g; see step (b) above) was added. The mixture was stirred for 3 h at 70° C. and then at 100° C. for an additional 22 h. The mixture was cooled to room temperature and the solvent evaporated under vacuum. Yield 80% of 2-Butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran.

Workup

waitat 100° C. for an additional 22 h
temperatureThe mixture was cooled to room temperature
customthe solvent evaporated under vacuum

Sources & evidence

ORD record: ord-5c581655555548d5b87176b54329fe21
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519165B2

Reaction notes

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