Nitric Acid → HCID 21479418, compound

HRID 2292694Notes

Reaction equation

HRID 2292694 reaction equation
[C:1]([C:5]1[C:13]2[S: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[S: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

4

Reactant 2

HCID 944Nitric AcidHCID 107041827-tert-butyl-2,3-dihydro-3,3-dimethylbenzothiophene

Product 1

HCID 21479418HCID 21479418, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzothiophene (4.0 g, 18.2 mmol) in glacial acetic acid (30 mL) is added dropwise 70% HNO3 (2.0 mL, 2.8 g, 31.8 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). Then the reaction mixture is partitioned between Et2O (50 mL) and H2O (2×50 mL). The ethereal layer is washed with saturated aqueous Na2CO3 (50 mL), dried (MgSO4), filtered and evaporated to a red solid. Crystallization from hexane provides the title compound as orange prisms. A second crop yielded slightly less pure material which is combined with the former and used without further purification.

Workup

  1. additionThe reaction mixture darkens to a deep green color over the course of the addition
  2. customThen the reaction mixture is partitioned between Et2O (50 mL) and H2O (2×50 mL)
  3. washThe ethereal layer is washed with saturated aqueous Na2CO3 (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to a red solid
  7. customCrystallization from hexane

Sources & evidence

ORD record
ord-42a1069991c540be9b5baa482e5fcc4c
Source dataset
uspto-grants-1997_11
Patent number
US05684041

Reaction notes

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