Synthesis Of Aromatic Aldehyde And Gelator's Design And Synthesis

This thesis gives an introduction of synthesis methods of aromatic aldehydes, anoverview of Low-molecular-mass Organic Gelators and proposes for dividing anddesigning gelator.Four aromatic aldehyde was synthesized through Gattermann-Koch reaction, suchas 3,4-dimethylbenzaldehyde, 2,4,6-trimethylbenzaldehyde, 2,4,5-trimethylbenzaldehydeand 5,6,7,8-tetrahydronaphthalene-2-carbaldehyde. The reactioncondition of 3,4-dimethylbenzaldehyde and 2,4,6-trimethylbenzaldehyde wasoptimized. The optimized condition of 3,4-dimethylbenzaldehyde is 0.024molconcentrated aqueous hydrochloride/1.0mol aluminum chloride, pressure (carbonmonoxide) 1.0~0.6MPa, 0°C, o-xylene/ AlCl3=5.0, 15h, yield 91.5%. The optimizedcondition of 2,4,6-trimethylbenzaldehyde is 0.037mol concentrated aqueoushydrochloride/1.0mol aluminum chloride, pressure (carbon monoxide)1.06~1.48MPa, 0°C, o-xylene/ AlCl3=3.08, 28h, yield 86.9%. And the reaction canbe promoted by 2-isopropyl ether, titanium(IV) chloride and aromatic aldehyde.In atomosphere Gattermann-Koch reaction, hydrochloride (gas) can besubstituted by concentrated aqueous hydrochloride in the synthesis of 3,4-dimethylbenzaldehyde.In addition, these aromatic aldehydes were used as material of condensation withD-sorbitol, which the product of condensation is a kind of Low-molecular-massOrganic Gelators. And six D-sorbitol acetal compound was synthesized,DBS(1,3:2,4-Dibenzylidene-D-sorbitol), MDBS (1,3:2,4-Di(4-methylbenzylidene)-D-sorbitol), DMDBS(1,3:2,4-Di(3,4-dimethylbenzylidene)-D-sorbitol), 2,4,6-TMDBS (1,3:2,4-Di(2,4,6-trimethylbenzylidene)-D-sorbitol), 2,4,5-TMDBS(1,3:2,4-Di(2,4,5-trimethylbenzylidene)-D-sorbitol), DTHNS (1,3:2,4-Di-(5,6,7,8-tetrahydronathalenyl-2-methylene)-D-sorbitol). In the experiment, thephenomenon is oberserved that the gelization property is different with differentsubstitute on bezene of DBS. The gelization property of 2,4,6-TMDBS is extremelypoor. However, DTHNS's gelization property is very good.Tewlevle carbamate and urea compounds were designed and synthesized; amongwhich compound 15,16,17,18 have good gelization property.