Sodium Chloride → 4-Methoxy-8-nitro-dibenzo[b,d]furan-1-carboxylic acid

HRID 2427855Notes

Reaction equation

HRID 2427855 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=3[C:7]=2[C:6]([CH:19]=[O:20])=[CH:5][CH:4]=1.[Cl-].[Na+].S(=O)(=O)([OH:25])N>O1CCOCC1.O>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=3[C:7]=2[C:6]([C:19]([OH:25])=[O:20])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 5987Sulfamic AcidHCID 211057134-Methoxy-8-nitro-dibenzofuran-1-carbaldehyde

Product 1

HCID 211057144-Methoxy-8-nitro-dibenzo[b,d]furan-1-carboxylic acidYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

4-Methoxy-8-nitro-dibenzofuran-1-carbaldehyde (1.03 g, 3.8 mmoles) is suspended in a mixture of dioxane (60 mL) and water (10 mL). Sodium chloride (0.445 g, 4.93 mmoles) and sulphamic acid (2.09 g, 21.6 mmoles) are added and the mixture is stirred at room temperature for 1 hour. The mixture is then diluted with water (100 mL) and extracted with AcOEt (200 mL). The organic layer is dried over Na2SO4 and the solvent is evaporated to yield 0.701 g of raw product which is employed in the next step without further purification.

Workup

  1. extractionextracted with AcOEt (200 mL)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-fe142767f768485a99360234d890cbdd
Source dataset
uspto-grants-2011_06
Patent number
US07968724B2

Reaction notes

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