Nitric Acid → 7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran
Reaction equation
[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17]>C(O)(=O)C>[C:1]([C:5]1[C:13]2[O:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
To a solution of 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran (10.0 g 49.0 mmol) in glacial acetic acid (80 mL) is added dropwise 70% HNO3 (4.0 mL, 5.7 g, 63.7 mmol). The reaction mixture darkens to a deep green color over the course of the addition. The reaction is monitored by TLC (2% EtOAc/hexanes), and is allowed to stir at 22° C. for 4 h. Then the reaction mixture is partitioned between Et2O (100 mL) and H2O (2×100 mL). The ethereal layer was washed with saturated aqueous Na2CO3 (50 mL), dried (MgSO4), filtered and evaporated to a red solid (9.12 g). Crystallization from hexane provides the title compound as orange prisms (2.26 g, 18.5%). A second crop yields slightly less pure material (4.93 g, 40.3%) which was used without further purification, mp=93°-94° C.
Workup
- additionThe reaction mixture darkens to a deep green color over the course of the addition
- customThen the reaction mixture is partitioned between Et2O (100 mL) and H2O (2×100 mL)
- washThe ethereal layer was washed with saturated aqueous Na2CO3 (50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated to a red solid (9.12 g)
- customCrystallization from hexane
Sources & evidence
- ORD record
- ord-806a51ded41a41f7add7f8b3d76c2f75
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05684041
Reaction notes
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