Synthesis of 1,2,3-trimethoxybenzene

Preparation of 1,2,3-trimethoxybenzene

Preparation of 1,2,3-trimethoxybenzene

Preparation of 1,2,3-trimethoxybenzene

20 g of pyrogallol are dissolved in 30 g of 35% aqueous sodium hydroxide in a 1-l round-bottomed flask closed with a cork, through which pass a thermometer and an open tube bent in a spiral to prevent spurting. 50 ml of dimethyl sulphate are gradually added with continuous shaking, the cork being momentarily removed. The temperature is not allowed to rise above 45° C. When heat is no longer evolved, the mixture is boiled under a reflux condenser, cooled, made alkaline with sodium hydroxide if necessary, the dark-coloured precipitate filtered at the pump, and well washed with water. It is dissolved in ether, filtered, the ether removed on a water bath, and the residue recrystallised from dilute alcohol. Yield 70% theoretical as colorless crystals; insoluble in water; soluble in alcohol and ether; m.p. 47° C; b.p. 235° C.

Systematic organic chemistry, by W. M. Cumming, 207-208, 1937.

IUPAC Name

1,2,3-trimethoxybenzene

InChI

InChI=1S/C9H12O3/c1-10-7-5-4-6-8(11-2)9(7)12-3/h4-6H,1-3H3

InChI Key

CRUILBNAQILVHZ-UHFFFAOYSA-N

Canonical SMILES

COC1=C(C(=CC=C1)OC)OC

MeSH Synonyms

1,2,3-TMB, 1,2,3-trimethoxybenzene

Depositor-Supplied Synonyms

1,2,3-TRIMETHOXYBENZENE, 634-36-6, Methylsyringol, Pyrogallol trimethyl ether, Tri-O-methylpyrogallol, Trimethoxybenzene, Benzene, 1,2,3-trimethoxy-, Benzene, trimethoxy-, CRUILBNAQILVHZ-UHFFFAOYSA-N, 3,4,5-Trimethoxybenzene, ST50406631, Methylsyringol (VAN), 1,3-Trimethoxybenzene, PubChem14319, ACMC-209nfl, AC1L1ZNC, AC1Q4FCR, bmse010218, UNII-MRE1O894FG, 1,2,3-trimethoxy benzene, MRE1O894FG, KSC308I8T, SCHEMBL151213, 137995_ALDRICH, 92159_FLUKA, CHEBI:86529, CRUILBNAQILVHZ-UHFFFAOYSA-, CTK2A8489, MolPort-001-761-442, HMS1577E02, ZINC152503, NSC10124, EINECS 211-207-2, ANW-34639, BBL003620, CT0050, NSC 10124, NSC-10124, STK499049, ZINC00152503, AKOS000120025, MCULE-7414816052, RL04415, RTR-021841, TRA0060424, 63744-60-5, AJ-12746, AK-94170, AN-20430, CJ-01156, KB-64216, OR011246, OR312367, ZB005183, AB0007116, AI3-02077, DB-003154, ST2408418, TL8004419, TR-021841, FT-0606231, A834379, AH-034/32464032, I01-4450, I01-7808, Q-200055, 3B3-030606, InChI=1/C9H12O3/c1-10-7-5-4-6-8(11-2)9(7)12-3/h4-6H,1-3H3

Removed Synonyms

Benzene,2,3-trimethoxy-, CID12462, T1102, M-3944

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