Synthesis of 1,4-dimethoxybenzene

Preparation of 1,4-dimethoxybenzene

 

Preparation of 1,4-dimethoxybenzene

Preparation of 1,4-dimethoxybenzene

 

The 1 mole of hydroquinone (benzene-1,4-diol, quinol) 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 solid reaction product is isolated by filtration, washed with water, and recrystallized from alcohol or vacuum distilled b.p. 109°C/20mm. Unchanged hydroquinone can be recovered by acidifying the aqueous reaction solution and the wash water and extracting them with ether. The yield of 4-methoxyphenol is 95%, b.p. 213 °C; b.p. 109°C/20mm; m.p. 54-56 °C.

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

IUPAC Name

1,4-dimethoxybenzene

InChI

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

InChI Key

OHBQPCCCRFSCAX-UHFFFAOYSA-N

Canonical SMILES

COC1=CC=C(C=C1)OC

MeSH Synonyms

1,4-dimethoxybenzene, 4-methoxyanisole, hydroquinone dimethyl ether, para-dimethoxybenzene

Depositor-Supplied Synonyms

1,4-Dimethoxybenzene, 150-78-7, p-Dimethoxybenzene, p-Methoxyanisole, HYDROQUINONE DIMETHYL ETHER, Benzene, p-dimethoxy-, Quinol dimethyl ether, Benzene, 1,4-dimethoxy-, Dimethylhydroquinone ether, Dimethyl ether hydroquinone, USAF AN-9, 4-Methoxyanisole, 1,4-Dimethoxybenzol, Anisole, p-methoxy-, USAF uctl-1791, Methyl p-methoxyphenyl ether, Dimethyl hydroquinone, 1,4-dimethoxy benzene, 1,4-dimethoxy-benzene, NSC 7483, Dimethylether hydrochinonu, Hydroquinone, dimethyl ether, UNII-24WC6T6X0G, FEMA No. 2386, CCRIS 5920, HSDB 4259, OHBQPCCCRFSCAX-UHFFFAOYSA-N, Dimethylether hydrochinonu [Czech], EINECS 205-771-9, SBB060067, DMB, AI3-24139, DSSTox_CID_2014, DSSTox_RID_76460, DSSTox_GSID_22014, CAS-150-78-7, p-dimethoxy benzene, 1,4-dimethoxy-benzen, AC1Q4FES, Benzene,1,4-dimethoxy-, AC1L1S4V, SCHEMBL8489, ACMC-1C1E3, Methyl 4-methoxyphenyl ether, WLN: 1OR DO1, KSC175M9L, MLS002454408, 4-Methoxyphenol, methyl ether, D131350_ALDRICH, W238600_ALDRICH, BENZENE,1,4-DIMETHOXY, 24WC6T6X0G, Jsp002876, CHEMBL1668604, SCHEMBL12015220, BDBM36302, CTK0H5695, NSC7483, MolPort-001-768-565, HMS2270C23, ZINC388747, NSC-7483, STR02500, WLN: T56 BNVNJ B1Q D1Q, 4-Methoxyanisole;Anisole, p-methoxy, Tox21_201333, Tox21_302782, ANW-21298, AR-1L1340, BBL003611, LS-878, MFCD00008401, STK065405, ZINC00388747, AKOS000119956, AS06962, MCULE-5232933383, RP20443, RTR-033046, TRA0083185, NCGC00091220-01, NCGC00091220-02, NCGC00091220-03, NCGC00256564-01, NCGC00258885-01, AJ-20759, AK109309, AN-23314, K896, KB-10592, OR034548, SMR001252207, ZB011683, 2-Benzimidazolinone,3-bis(hydroxymethyl)-, AB1003116, DB-013768, ST2403009, TR-033046, 2-Benzimidazolinone, 1,3-bis(hydroxymethyl), D0629, FT-0606887, ST51046314, T7424, TL80073944, Dimethylhydroquinone; Hydroquinone dimethyl ether, 3B4-2765, Hydroquinone dimethyl ether (1,4-Dimethoxybenzene), I14-7639, W-108072, InChI=1/C8H10O2/c1-9-7-3-5-8(10-2)6-4-7/h3-6H,1-2H, HYDROQUINONE DIMETHYL ETHER (SEE ALSO: HYDROQUINONE MONOMETHYL ETHER (CAS 150-76-5))

Removed Synonyms

Dimethylhydroquinone, Benzene,4-dimethoxy-, Dimethylolbenzimidazolon, 2-BENZIMIDAZOLINONE, C8H10O2, CID9016, 1,3-Bis(hydroxymethyl)-2-benzimidazolinone, 15301-67-4

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