4-Hydroxybenzaldehyde → 2,3-Bis(2-formylphenoxy)-propan-1-ol
Reaction equation
[OH-:1].[Na+].O[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.Br[CH:13]([CH2:16]Br)[CH2:14][OH:15].[OH2:18]>>[OH:15][CH2:14][CH:13]([O:18][C:6]1[CH:5]=[CH:4][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])[CH2:16][O:1][C:10]1[CH:11]=[CH:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]Participants
5
Procedure
To water (150 mL) to which 17 g of 50% sodium hydroxide have been added, is added p-hydroxybenzaldehyde (24.4 g, 0.20 m), followed by 2,3-dibromopropanol (21.8 g, 0.10 m). The mixture is heated at reflux for 6 hours and allowed to cool which results in crystallization of the product, which is collected by filtration, washed with water, and dried in air. The yield is 23 g (76.7% of the theoretical yield) of 4,4'-[(1-(hydroxymethyl)-1,2-ethanediyl]bis(oxy)bis[benzaldehyde] as indicated by mass spectrum analysis. A mixture of the bis-aldehyde (3.0 g, 0.01 m), ethyl cyanoacetate (2.26 g, 0.02 m), N,N-dimethylformamide and 10 drops piperidine is heated for 4 hours at about 80° C. and then drowned into methanol (200 mL). The product crystallizes upon cooling to room temperature and is collected by filtration, washed with ethanol and dried in air (yield--2.1 g). The product has an absorption maximum at 339 nm in methylene chloride and has the following structure as evidenced by mass spectroscopy analysis. ##STR28##