Synthesis of 3,4-dimethoxybenzaldehyde

Preparation of 3,4-dimethoxybenzaldehyde

Preparation of 3,4-dimethoxybenzaldehyde

Preparation of 3,4-dimethoxybenzaldehyde

The 1 mole of 3-methoxy-4-hydroxybenzaldehyde (vanillin) is treated rapidly with stirring, in a three-necked flask provided with a reflux condenser, stirrer, internal thermometer, and dropping funnel, with 1.25 mole of 10% sodium hydroxide. With vigorous stirring, 1 mole of dimethyl sulfate is added in such a way that the temperature remains below 40° C (water cooling). To complete the reaction and to destroy unchanged dimethyl sulfate, the mixture is then heated for 30 min on a boiling water bath (to keep the sodium salt of vanillin permanently in solution, the reaction is performed on a boiling water bath). After cooling, in the case of liquid products the organic layer is separated off and the aqueous solution is extracted several times with ether. The combined organic phases are washed with dilute sodium carbonate and then with water, dried with calcium chloride, and fractionated b.p. 153 °C/8mm or solid reaction product is isolated by filtration, washed with water, and recrystallized from ligroin. Unchanged 3-methoxy-4-hydroxybenzaldehyde (vanillin) can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 3,4-dimethoxybenzaldehyde is 70%, b.p. 281 °C; m.p. 40-43 °C;

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 206-207, (1973)

IUPAC Name

3,4-dimethoxybenzaldehyde

InChI

InChI=1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3

InChI Key

WJUFSDZVCOTFON-UHFFFAOYSA-N

Canonical SMILES

COC1=C(C=C(C=C1)C=O)OC

MeSH Synonyms

veratraldehyde

Depositor-Supplied Synonyms

3,4-Dimethoxybenzaldehyde, VERATRALDEHYDE, 120-14-9, Veratric aldehyde, Vanillin methyl ether, Methylvanillin, Veratral, Veratryl aldehyde, Benzaldehyde, 3,4-dimethoxy-, Veratrum aldehyde, 3,4-Dimethoxy benzaldehyde, p-Veratric aldehyde, 4-O-Methylvanillin, 3,4-Dimethoxybenzenecarbonal, Protocatechualdehyde dimethyl ether, Protocatechuic aldehyde dimethyl ether, 3,4-DIMETHOXY-BENZALDEHYDE, Protocatechuecaldehyde dimethyl ether, NSC 24521, UNII-UI88P68JZD, FEMA No. 3109, CCRIS 6285, CHEBI:17098, WJUFSDZVCOTFON-UHFFFAOYSA-N, EINECS 204-373-2, BRN 0473899, AI3-08099, Benzaldehyde,4-dimethoxy-, DSSTox_CID_6285, Veratraldehyde-2-13C, DSSTox_RID_78087, DSSTox_GSID_26285, WLN: VHR CO1 DO1, CAS-120-14-9, PubChem8238, VERATRYLALDEHYDE, 3,4dimethoxybenzaldehyde, AC1L1QYK, AC1Q4FDU, 3,4 dimethoxybenzaldehyde, 4,3-dimethoxybenzaldehyde, ACMC-209a6e, bmse010220, 3, 4-Dimethoxybenzaldehyde, UI88P68JZD, SCHEMBL25202, KSC175E8J, W310905_ALDRICH, 143758_ALDRICH, AC1Q46T0, CHEMBL1088937, 94860_FLUKA, CTK0H5284, FEMA 3109, TIMTEC-BB SBB040236, NSC8500, MolPort-000-871-214, OTAVA-BB 1180632, 3,4-DIMETHOXYBENZALDEHHYDE, BB_NC-2052, ZINC155456, ACT06905, NSC-8500, NSC24521, AKOS BBS-00003208, Tox21_201566, Tox21_303074, ANW-17460, AR-1L8134, BBL010373, LABOTEST-BB LT00235863, LABOTEST-BB LT03331050, LS-628, MFCD00003363, NSC-24521, SBB040236, STK188425, Vanillin methyl ether; Veratraldehyde, ZINC00155456, AKOS000118989, AS02987, CM13990, MCULE-1202068347, NE10275, RP22905, RTC-010113, TRA0003531, NCGC00091642-01, NCGC00091642-02, NCGC00091642-03, NCGC00257217-01, NCGC00259115-01, 4CN-0811, AJ-13584, AK-46721, AN-22815, BC622797, BR-46721, CJ-01437, KB-28345, OR025647, OR208289, SC-00570, TL806334, ZB006061, 3,4-dimethoxybenzaldehyde (veratraldehyde), AB1000043, DB-014213, ST2410267, TC-010113, AM20050100, D0507, FT-0600118, ST45169641, C02201, 107052-EP2295423A1, 107052-EP2298744A2, 107052-EP2374783A1, 107052-EP2377841A1, AH-034/32845024, I01-2283, W-108485, 3B3-077372, InChI=1/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H

Removed Synonyms

Methyl vanillin, C9H10O3, CID8419, H0850, 4-08-00-01765 (Beilstein Handbook Reference), 12070-07-4

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