**APAAN** (alpha-Phenylacetoacetonitrile) starting from **benzylnitrile** and **ethyl ethanoate (ethyl acetate)** in the presence of **sodium ethoxide**:
### Reagents:
- Benzylnitrile (C₆H₅CH₂CN)
- Ethyl ethanoate (Ethyl acetate, CH₃COOCH₂CH₃)
- Sodium ethoxide (NaOEt)
- Ethanol (as solvent)
- Hydrochloric acid (HCl) for neutralization
- Ice for cooling
### Equipment:
- Round-bottom flask (2 L or as appropriate for the scale)
- Magnetic stirrer with hotplate
- Reflux condenser
- Dropping funnel
- Separation funnel
- Ice bath
- pH meter or indicator paper
- Vacuum filtration setup
### Reaction Overview:
The reaction between **benzylnitrile** and **ethyl ethanoate** forms APAAN through a Claisen condensation, using **sodium ethoxide** as the base catalyst.
### Step-by-Step Procedure:
#### 1. Preparation of Sodium Ethoxide:
- In a fume hood, take **sodium metal** (or commercially available sodium ethoxide) and **ethanol**.
- Slowly add **small pieces of sodium metal** (be cautious of reactivity) to **dry ethanol** in a **dry round-bottom flask** equipped with a magnetic stirrer. This will generate sodium ethoxide and hydrogen gas (be careful).
- Use **0.1 mol sodium metal** per **0.1 mol of benzylnitrile**.
- Once all sodium metal is dissolved and reacted, you now have **sodium ethoxide** solution.
**Example**:
For 0.1 mol of benzylnitrile:
- 0.1 mol sodium = 2.3 g
- 0.1 mol ethanol = 4.6 g (approx. 5.8 mL of ethanol)
#### 2. Setting up Reaction:
- In a clean **round-bottom flask**, add **benzylnitrile** (0.1 mol, 11.8 g).
- Add **ethyl ethanoate** (0.12 mol, 12.5 g) into the same flask.
- Add your **freshly prepared sodium ethoxide** solution from step 1 into the flask.
- Attach a reflux condenser to the flask to prevent loss of solvent during heating.
- Place the flask on a **magnetic stirrer** and heat gently to maintain **reflux** for **4-6 hours** at around **60-70°C**.
#### 3. Monitoring the Reaction:
- After 4-6 hours of refluxing, cool the reaction mixture down to **room temperature**.
- Use **TLC (Thin Layer Chromatography)** to monitor the completion of the reaction if possible, or use the color change and solubility properties to check completion (the reaction mixture should become more viscous).
#### 4. Quenching the Reaction:
- Once the reaction is complete, the reaction mixture must be **quenched** by adding **diluted hydrochloric acid (HCl)** (1M) dropwise while keeping the flask cooled in an **ice bath**.
- Add **enough HCl** until the reaction mixture becomes neutral (pH 7) or slightly acidic (pH 5-6). Monitor the pH using pH paper or a meter.
- The addition of HCl will neutralize the excess sodium ethoxide and stop the reaction.
#### 5. Extraction:
- After quenching, transfer the mixture to a **separatory funnel**.
- Add an organic solvent like **dichloromethane (DCM)** or **ethyl acetate** to extract the organic product.
- Shake and allow the layers to separate.
- Drain the aqueous layer, and wash the organic layer with **brine (salt water)** to remove residual water.
- Separate the organic layer and dry over **anhydrous sodium sulfate**.
#### 6. Evaporation of Solvent:
- Once the organic layer is dry, filter the solution to remove the drying agent (sodium sulfate).
- Use a **rotary evaporator** to remove the organic solvent, yielding crude **APAAN**.
#### 7. Purification:
- The crude APAAN product can be purified by **recrystallization** from a suitable solvent like ethanol or by **vacuum distillation** if needed, depending on the purity required.
#### Yield:
- The typical yield for this reaction should be between **70-85%** depending on the purity of reagents and reaction conditions.
### Safety Precautions:
- **Sodium ethoxide** is highly reactive, so handle with care, especially around moisture.
- Always perform reactions involving sodium metal and flammable solvents like ethanol in a **fume hood** with proper ventilation.
- Wear proper protective gear, including gloves and eye protection.
### Conclusion:
This process describes the production of **APAAN** from **benzylnitrile** and **ethyl ethanoate** using **sodium ethoxide** as a catalyst in a Claisen condensation reaction, followed by neutralization and extraction to obtain the desired product.
### Reagents:
- Benzylnitrile (C₆H₅CH₂CN)
- Ethyl ethanoate (Ethyl acetate, CH₃COOCH₂CH₃)
- Sodium ethoxide (NaOEt)
- Ethanol (as solvent)
- Hydrochloric acid (HCl) for neutralization
- Ice for cooling
### Equipment:
- Round-bottom flask (2 L or as appropriate for the scale)
- Magnetic stirrer with hotplate
- Reflux condenser
- Dropping funnel
- Separation funnel
- Ice bath
- pH meter or indicator paper
- Vacuum filtration setup
### Reaction Overview:
The reaction between **benzylnitrile** and **ethyl ethanoate** forms APAAN through a Claisen condensation, using **sodium ethoxide** as the base catalyst.
### Step-by-Step Procedure:
#### 1. Preparation of Sodium Ethoxide:
- In a fume hood, take **sodium metal** (or commercially available sodium ethoxide) and **ethanol**.
- Slowly add **small pieces of sodium metal** (be cautious of reactivity) to **dry ethanol** in a **dry round-bottom flask** equipped with a magnetic stirrer. This will generate sodium ethoxide and hydrogen gas (be careful).
- Use **0.1 mol sodium metal** per **0.1 mol of benzylnitrile**.
- Once all sodium metal is dissolved and reacted, you now have **sodium ethoxide** solution.
**Example**:
For 0.1 mol of benzylnitrile:
- 0.1 mol sodium = 2.3 g
- 0.1 mol ethanol = 4.6 g (approx. 5.8 mL of ethanol)
#### 2. Setting up Reaction:
- In a clean **round-bottom flask**, add **benzylnitrile** (0.1 mol, 11.8 g).
- Add **ethyl ethanoate** (0.12 mol, 12.5 g) into the same flask.
- Add your **freshly prepared sodium ethoxide** solution from step 1 into the flask.
- Attach a reflux condenser to the flask to prevent loss of solvent during heating.
- Place the flask on a **magnetic stirrer** and heat gently to maintain **reflux** for **4-6 hours** at around **60-70°C**.
#### 3. Monitoring the Reaction:
- After 4-6 hours of refluxing, cool the reaction mixture down to **room temperature**.
- Use **TLC (Thin Layer Chromatography)** to monitor the completion of the reaction if possible, or use the color change and solubility properties to check completion (the reaction mixture should become more viscous).
#### 4. Quenching the Reaction:
- Once the reaction is complete, the reaction mixture must be **quenched** by adding **diluted hydrochloric acid (HCl)** (1M) dropwise while keeping the flask cooled in an **ice bath**.
- Add **enough HCl** until the reaction mixture becomes neutral (pH 7) or slightly acidic (pH 5-6). Monitor the pH using pH paper or a meter.
- The addition of HCl will neutralize the excess sodium ethoxide and stop the reaction.
#### 5. Extraction:
- After quenching, transfer the mixture to a **separatory funnel**.
- Add an organic solvent like **dichloromethane (DCM)** or **ethyl acetate** to extract the organic product.
- Shake and allow the layers to separate.
- Drain the aqueous layer, and wash the organic layer with **brine (salt water)** to remove residual water.
- Separate the organic layer and dry over **anhydrous sodium sulfate**.
#### 6. Evaporation of Solvent:
- Once the organic layer is dry, filter the solution to remove the drying agent (sodium sulfate).
- Use a **rotary evaporator** to remove the organic solvent, yielding crude **APAAN**.
#### 7. Purification:
- The crude APAAN product can be purified by **recrystallization** from a suitable solvent like ethanol or by **vacuum distillation** if needed, depending on the purity required.
#### Yield:
- The typical yield for this reaction should be between **70-85%** depending on the purity of reagents and reaction conditions.
### Safety Precautions:
- **Sodium ethoxide** is highly reactive, so handle with care, especially around moisture.
- Always perform reactions involving sodium metal and flammable solvents like ethanol in a **fume hood** with proper ventilation.
- Wear proper protective gear, including gloves and eye protection.
### Conclusion:
This process describes the production of **APAAN** from **benzylnitrile** and **ethyl ethanoate** using **sodium ethoxide** as a catalyst in a Claisen condensation reaction, followed by neutralization and extraction to obtain the desired product.