Mesitylene → 3-Allyl-4-hydroxy-5-methoxy-benzaldehyde
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11]CC=C)[CH:6]=[O:7].[OH-].[Na+].[C:17]1(C)[CH:22]=C(C)C=C(C)[CH:18]=1>>[CH2:22]([C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[OH:11])[CH:6]=[O:7])[CH:17]=[CH2:18]Participants
4
Procedure
3-Methoxy-4-(2-propenyloxy)benzaldehyde (19.7 g, 0.100 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.