2,2’-(1,3-Propanediyldioxy)bisbenzaldehyde synthesis
- Product Name:2,2’-(1,3-Propanediyldioxy)bisbenzaldehyde
- CAS Number:17954-12-0
- Molecular formula:C17H16O4
- Molecular Weight:284.31
Yield:17954-12-0 95%
Reaction Conditions:
Stage #1: salicylaldehydewith potassium hydroxide in tetrahydrofuran;dimethyl sulfoxide; for 0.5 h;Reflux;
Stage #2: 1,3-dibromo-propane in tetrahydrofuran;dimethyl sulfoxide; for 16 h;Reflux;
Steps:
General procedure for synthesis of compounds1a-1c
General procedure: Salicylaldehyde (200 mmol), KOH (240 mmol), 50 cm3THF, and 10 cm3 DMSO were placed in a 250 cm3 twoneckedround-bottom flask provided with a reflux condenser.The obtained mixture was refluxed for 30 minunder continuous stirring. A solution of 100 mmol of 1,2-dibromoethane, 1,3-dibromopropane, or 1,4-dibromobutanewas dissolved in 10 cm3 of THF/DMSO (9:1) andadded slowly to the reaction mixture using a droppingfunnel. After the addition, the mixture was kept underreflux for 16 h. After completion of the reaction [monitoredby TLC using ethyl acetate/hexane (1:3 v/v)], the resultingmixture was cooled to room temperature and washed with250 cm3 water. The pale yellow precipitate was filtered offand recrystallized in ethanol to afford pure products 1a-1bas colorless crystalline solids. (1a: 25 g, yield: 92%; 1b:27 g, yield: 95%; 1c: 28.8 g, yield: 97%) [22, 23].
References:
Darabi, Hossein Reza;Rastgar, Saeed;Aghapoor, Kioumars;Mohsenzadeh, Farshid [Monatshefte fur Chemie,2018,vol. 149,# 6,p. 1121 - 1124]
90-02-8
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