Reaction #833513

Reaction equation

3-Ethoxy-4-(2-propenyloxy)benzaldehyde

sodium hydroxide

mesitylene

→

3-allyl-5-ethoxy-4-hydroxybenzaldehyde

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   WashThe aqueous phase was washed two times with diethyl ether
3. 3
   Extractionextracted with ethyl acetate
4. 4
   OtherAfter drying
5. 5
   Concentrationconcentrating the organic phase, there
6. 6
   Otherthat crystallized
7. 7
   Temperatureon cooling

Procedure

3-Ethoxy-4-(2-propenyloxy)benzaldehyde (20.0 g, 0.087 mol) was heated under reflux in 75 ml mesitylene (1,3,5-trimethylbenzene) for 20 hours. After cooling, 250 ml 2N sodium hydroxide were added to the reaction mixture. The aqueous phase was washed two times with diethyl ether. The aqueous phase was subsequently acidified with concentrated hydrochloric acid under ice cooling and then extracted with ethyl acetate. After drying and concentrating the organic phase, there remained a light orange-colored oil that crystallized on cooling.

Source