Water → (2-Butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone

HRID 1897859Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:3]=1.[N+:17]([C:20]1[CH:25]=[CH:24][C:23](ON)=[CH:22][CH:21]=1)([O-:19])=[O:18].O>C(O)(=O)C>[CH2:11]([C:10]1[O:15][C:23]2[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][C:22]=2[C:9]=1[C:8](=[O:16])[C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH2:12][CH2:13][CH3:14]

Participants

Conditions

Temperature: 115 °C

Procedure

1-(4-hydroxyphenyl)-1,3-heptandione, 697 g, is dissolved in 2532 g acetic acid. O-(4-Nitrophenyl)hydroxylamine, 488 g, is added in portions at ca 20° C. The formed slurry is diluted with 739 g acetic acid and the mixture heated to 115° C. and stirred for 3 h. The dark solution is cooled and 1635 g water is added keeping the temperature at 70-80° C. The temperature is adjusted to 60° C. and seeding crystals are added. When crystallisation has started, the slurry is cooled to 4° C., filtered and washed with 870 g of 67% aqueous acetic acid followed by 580 g water. Drying at reduced pressure at 70° C. gives 736 g 2-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran. Yield 69%.

Workup

temperatureThe dark solution is cooled
customat 70-80° C
customis adjusted to 60° C.
additionseeding crystals are added
customWhen crystallisation
temperaturethe slurry is cooled to 4° C.
filtrationfiltered
washwashed with 870 g of 67% aqueous acetic acid
customDrying at reduced pressure at 70° C.

Sources & evidence

ORD record: ord-35e5410d1fdc4f5f9aa2f47b62f10e9e
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519165B2

Reaction notes

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