video tutorial Ethyl chloroacetate preparation

Summary: Synthesis of Ethyl Chloroacetate

• Objective: esterify chloroacetic acid with ethanol using sulfuric acid as a catalyst; test an experimental method to remove water during reflux to improve efficiency.
• Setup & reagents: chloroacetic acid dissolved in ethanol (150 mL, ~3x molar excess) in a 500 mL flask; catalyst added (3 mL concentrated sulfuric acid); reflux started.
• Water removal attempt: attempted to distill the ethanol–water azeotrope during reflux using a filter setup with calcium oxide to trap water and allow dry ethanol to drip back; multiple configurations tested but caused overflow and calcium oxide to enter the reaction mixture.
• Alternate approach: after issues with the water-removal setup, switched to simple distillation, first removing excess ethanol, then collecting fractions at increasing temperatures (above 100°C and above 135°C).
• Workup: organic layer separated from a water–ethyl chloroacetate mixture; washed with water; dried with anhydrous magnesium sulfate.
• Product yield: 55 g of ethyl chloroacetate obtained, corresponding to a 57% yield based on starting chloroacetic acid.
• Product notes: ethyl chloroacetate is lachrymatory and more irritating than benzoyl chloride; handle with care.
• Safety considerations: chloroacetic acid is toxic/metabolic poison; avoid skin contact; eye and respiratory hazards from the product.
• Potential improvements: calcium oxide–based drying/esterification approach might improve efficiency but requires specialized equipment and solid-granule oxide to prevent loss into the reaction mixture.