Nitric Acid → 7-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

HRID 2292483Notes

Reaction equation

HRID 2292483 reaction equation
[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([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].CCCCCC>C(O)(=O)C>[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([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

5

Reactant 3

HCID 944Nitric AcidHCID 8058HexaneHCID 11805831HCID 11805831, compound

Product 1

HCID 107531427-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
24 °C

Procedure

A solution of 7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan (10.0 g, 49.0 mmol) in glacial acetic acid 80 mL) is treated with 70% nitric acid (4.0 mL, 63.7 mmol) dropwise, and allowed to stir at 24° C. for 4 h. TLC (hexane) is used to monitor reaction progress. The reaction mixture is partitioned between Et2O (100 mL) and H2O (100 mL). The Et2O layer is washed with H2O (50 mL) and saturated Na2 CO3 (50 mL), dried (MgSO4), filtered and evaporated to a red solid (9.12 g). Crystallization from hexane provides 7-tert-butyl-3,3-dimethyl-5-nitro-2,3-dihydrobenzo[b]furan as an orange solid.

Workup

  1. customreaction progress
  2. customThe reaction mixture is partitioned between Et2O (100 mL) and H2O (100 mL)
  3. washThe Et2O layer is washed with H2O (50 mL) and saturated Na2 CO3 (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to a red solid (9.12 g)
  7. customCrystallization from hexane

Sources & evidence

ORD record
ord-f6ad421a5c99424eb18fbb7e820671a8
Source dataset
uspto-grants-1997_11
Patent number
US05684002

Reaction notes

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