Synthesis of 1,3-dimethoxybenzene

Preparation of 1,3-dimethoxybenzene

Preparation of 1,3-dimethoxybenzene

Preparation of 1,3-dimethoxybenzene

The 1 mole of resorcinol is treated rapidly with stirring, in a three-necked flask provided with a reflux condenser, stirrer, internal thermometer, and dropping funnel, with 2.5 mole of 10% sodium hydroxide. With vigorous stirring, 2 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. After cooling, 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. Unchanged resorcinol can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 1,3-dimethoxybenzene is 85%, b.p. 85-87 °C/7 mm; b.p. 110°C/20mm; n20/D 1.524; d=1.055 g/mL at 25 °C;

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

IUPAC Name

1,3-dimethoxybenzene

InChI

InChI=1S/C8H10O2/c1-9-7-4-3-5-8(6-7)10-2/h3-6H,1-2H3

InChI Key

DPZNOMCNRMUKPS-UHFFFAOYSA-N

Canonical SMILES

COC1=CC(=CC=C1)OC

MeSH Synonyms

1,3-dimethoxybenzene, meta-dimethoxybenzene

Depositor-Supplied Synonyms

1,3-Dimethoxybenzene, 151-10-0, M-DIMETHOXYBENZENE, Resorcinol dimethyl ether, Benzene, 1,3-dimethoxy-, 3-Methoxyanisole, Benzene, m-dimethoxy-, 1,3-dimethoxybenzol, m-Methoxyanisole, Dimethylresorcinol, Dimethyl resorcinol, Methoxyanisole, m-, 1,3-Dimethoxy-benzene, Dimethylether resorcinolu, UNII-2694Z07HQY, 1,3-DIMETHOXY BENZENE, FEMA No. 2385, Dimethylether resorcinolu [Czech], DPZNOMCNRMUKPS-UHFFFAOYSA-N, NSC 8699, EINECS 205-783-4, SBB060066, AI3-00845, m-dimethoxy-benzene, m-Dimethoxy benzene, Benzene,3-dimethoxy-, 1,3-Dimethoxy bengene, ACMC-1BZ9C, AC1L1S5J, AC1Q4FF5, SCHEMBL9350, DSSTox_CID_27060, DSSTox_RID_82077, DSSTox_GSID_47060, KSC490I7T, W238503_ALDRICH, 126306_ALDRICH, CHEMBL2252486, SCHEMBL13322163, 83610_FLUKA, CTK3J0479, RESCORCINOL DIMETHYL ETHER, NSC8699, MolPort-001-757-279, 2694Z07HQY, KST-1B2729, ZINC388167, ACT07566, NSC-8699, STR00616, 151-10-0 1,3-dimethoxybenzene, Tox21_302348, ANW-21313, AR-1B6952, MFCD00008384, WT2100, ZINC00388167, AKOS000120162, M-DIMETHOXYBENZENE;FEMA 2385, AS06961, CS19845, MCULE-9933889768, RP15884, RTC-066557, TRA0062283, NCGC00256016-01, AJ-20466, AK-91612, AN-23320, CAS-151-10-0, CJ-03139, KB-10401, LS-29870, OR034614, OR252272, SC-26918, ZB011331, DB-013763, ST2408457, TC-066557, TL8001104, D0628, FT-0606678, ST51046313, M-3935, 3B4-3495, I01-8956, I14-5192, W-108064, InChI=1/C8H10O2/c1-9-7-4-3-5-8(6-7)10-2/h3-6H,1-2H

Removed Synonyms

Benzene, dimethoxy-, BUTYL RICINOLEATE, C8H10O2, CID9025, 28906-96-9, 27598-81-8, 28000-65-9, propan-2-yl 4-(2-{butyl[(propan-2-yloxy)carbonyl]amino}ethyl)piperazine-1-carboxylate hydrochloride(1:1)

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