Hydrochloric Acid → 3-Nitro-trans-stilbene

HRID 2086772Notes

Reaction equation

HRID 2086772 reaction equation
[H-].[Na+].[CH2:3](P(=O)(OCC)OCC)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O)([O-:20])=[O:19].Cl>CN(C)C=O>[N+:18]([C:21]1[CH:22]=[C:23](/[CH:24]=[CH:3]/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:26]=[CH:27][CH:28]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydride

Product 1

HCID 9775603-Nitro-trans-stilbeneYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 1.48 g) in N,N-dimethylformamide (40 ml) was added a solution of diethyl benzylphosphonate (7.69 g) in N,N-dimethylformamide (40 ml) at 0° C. The mixture was stirred at room temperature for 30 minutes, then a solution of 3-nitrobenzaldehyde (5.09 g) was added thereto. After stirring at 50° C. for 1 hour, the mixture was poured into dilute hydrochloric acid, and extracted with ethyl acetate 3 times. The combined organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give (E)-3-nitrostilbene (3.97 g).

Workup

  1. stirringAfter stirring at 50° C. for 1 hour
  2. extractionextracted with ethyl acetate 3 times
  3. washThe combined organic solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-bf31108c068348599048d8e61d2be56c
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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