4-(2,4-Dimethyl-3-nitrophenyl)butanoic acid → 5,7-Dimethyl-6-nitro-3,4-dihydronaphthalen-1(2H)-one

HRID 1662281Notes

Reaction equation

[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O>O>[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[C:4]2[C:3]=1[CH2:12][CH2:13][CH2:14][C:15]2=[O:17]

Participants

Conditions

Temperature: 110 °C

Procedure

PPA (100 g) was warmed to 110° C. and 4-(2,4-dimethyl-3-nitrophenyl)butanoic acid (3.04 g, 12.8 mmol) was added. The resulting solid slowly turn to a brown solution. The reaction was stirred at 110° C. for 4 hours, then poured into 200 ml of water with strong stirring. The mixture was extracted with dichloromethane (×3), and the organic solution was dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by Biotage (hexane/EtOAc, 0-30%, 40 min) to give pure compounds as yellow solid (2 g, 71%).

Workup

extractionThe mixture was extracted with dichloromethane (×3)
dry with materialthe organic solution was dried over anhydrous Na2SO4
customevaporated to dryness
customThe residue was purified by Biotage (hexane/EtOAc, 0-30%, 40 min)

Sources & evidence

ORD record: ord-477fee288686431e87e0bc315b9802a0
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030518B2

Reaction notes

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