M-Xylene → 2-Nitro-2',4'dimethyl benzophenone
Reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[C:13]1([CH3:20])[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1.[OH-].[K+]>[Cr].[Co]>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([C:18]1[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[CH3:20])=[O:8])([O-:3])=[O:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2-Nitrobenzoic acid (16.7 g, 0.1 mol) and m-xylene (11.7 g, 0.11 mol) were charged in a 300 cc Hastelloy-C autoclave. The reaction mixture was heated to 50° C. and stirred for 3 hours. Most of the HF was vented through a KOH scrubber and the product was transferred to a flask containing ice (100 g). The contents of the flask were neutralized to a pH=7. A brown solid (11.5 g) precipitated which was removed via filtration and discarded. The filtrate was extracted with ethyl acetate (2×100 mL). The ethyl acetate layer was dried and concentrated to afford the product (94% pure) (9.7 g, 35% yield) of 2-nitro-2',4'dimethyl benzophenone. A small portion (5.0 g) of the product was purified via Kugelrohr distillation to afford a yellow solid (4.2 g); m.p. 78°-80° C.
Workup
- customthe product was transferred to a flask
- customA brown solid (11.5 g) precipitated which
- customwas removed via filtration
- extractionThe filtrate was extracted with ethyl acetate (2×100 mL)
- dry with materialThe ethyl acetate layer was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-70ceddf2a95b48dab3e06b00e9eed7f7
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05130448
Reaction notes
Loading…