Acetic Anhydride → 1-(2-Nitroethenyl)-4-phenoxybenzene

HRID 1693792Notes

Reaction equation

HRID 1693792 reaction equation
[N+:1]([CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)[O-])([O-:3])=[O:2].[Na+].C(OC(=O)C)(=O)C.C(N(CC)CC)C>O1CCCC1>[N+:1](/[CH:4]=[CH:5]/[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 66707614Sodium 2-nitro-1-(4-phenoxy-phenyl)ethanolate

Product 1

HCID 190824071-(2-Nitroethenyl)-4-phenoxybenzeneYield 139.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium 2-nitro-1-(4-phenoxy-phenyl)-ethanolate (1.17 g, 4.16 mmol) described in Manufacturing Example 17-1-1, acetic anhydride (510 mg, 4.99 mmol) and triethylamine (696 μL, 4.99 mmol) in anhydrous tetrahydrofuran (20 mL) was stirred overnight under nitrogen atmosphere at room temperature. The reaction mixture was partitioned into water and ethyl acetate at room temperature. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure to obtain the title compound (1.4 g, 70%, purity: ca. 50%) as a crude product.

Workup

  1. customThe reaction mixture was partitioned into water and ethyl acetate at room temperature
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-6a20c9c3a2524622a1a21eb985b756a9
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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