Reaction #2028887

Reaction equation

hydrochloric acid

Ethyl formate

4′-chloroacetophenone

Sodium methoxide

→

yellow oil

Yield 100.2%

3-[4-(chloro)phenyl]-propane-1,3-dione

Yield 100.2%

Solvents

ether

Conditions

Workup

1. 1
   OtherThe phases were separated
2. 2
   Washthe ethereal solution washed with brine
3. 3
   Dryingdried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo

Procedure

Ethyl formate (8.15 g, 0.11 mol) and 4′-chloroacetophenone (15.4 g, 0.1 mol) were stirred in ether (150 mL) at room temperature. Sodium methoxide (25%) (23.77 g, 0.11 mol) was added dropwise. The mixture was stirred at room temperature for 16 hours and was then treated with 150 mL of 1N hydrochloric acid. The phases were separated and the ethereal solution washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford 18.3 g of a yellow oil. The resulting crude mixture was used directly in the next step without purification.

Source