Reaction #51866

Reaction equation

(3,4-dichloro-phenoxy)-acetic acid

allyl alcohol

→

title compound

Yield 96.8%

(3,4-Dichloro-phenoxy)acetic acid allyl ester

Yield 96.8%

Conditions

Workup

1. 1
   Concentrationconcentrated sulfuric as a catalyst
2. 2
   Otherthe volatile fractions removed in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl ether (50 cm3)
4. 4
   Washwashed with water (25 cm3)
5. 5
   Washwashed with saturated sodium bicarbonate (25 cm3)
6. 6
   Washwashed with brine (25 cm3)
7. 7
   Dryingdried over magnesium sulfate, vacuum
8. 8
   Filtrationfiltered
9. 9
   Otherthe filtrate volatile fractions removed in vacuo

Procedure

To a solution of commercially available (3,4-dichloro-phenoxy)-acetic acid (2.65 g, 12.0 mmol) in allyl alcohol (12.0 cm3, 180 mmol) at ambient temperature under an atmosphere of dry nitrogen was added 4 drops concentrated sulfuric as a catalyst. The solution was stirred at ambient temperature for 20 hours and the volatile fractions removed in vacuo. The residue was dissolved in ethyl ether (50 cm3), washed with water (25 cm3), washed with saturated sodium bicarbonate (25 cm3), washed with brine (25 cm3), dried over magnesium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to afford the title compound as a colorless viscous oil (3.02 g, 96.8%) with positive ion ESI (M+H)+261.3.

Source