Orcinol monomethyl ether

Submitted by R. N. Mirrington and G. I. Fentrill1 Checked by H. Gurien, G, Kaplan, and A. Brossi 

Orcinol Dimethyl Ether. In a 1-1. three-necked flask fitted with a mechanical stirrer, a condenser, and a 100-ml. dropping funnel are placed 124 g. (0.9 mole) of anhydrous 

Cautionl Because hydrogen is evolved and large volumes of foul-smelling ethyl methyl sulfide are liberated, this step should be conducted in a well-ventilated hood. 

Orcinol Monomethyl Ether. In a 1-1. three-necked flask equipped with a magnetic stirrer, a condenser, a dropping funnel, and a nitrogen inlet are placed 250 ml. of dry dimethyl-formamide (Note 6) and 22 g. (0.55 mole) of sodium hydride (60% oil dispersion). The suspension is stirred under an atmosphere of dry nitrogen and cooled with an ice bath while a solution of 31 g. (37 ml., 0.50 mole) of ethanethiol (Note 7) in 150 ml. of dry dimethylformamide (Note 6) is added slowly from the dropping funnel over a period of 20 minutes. The ice bath is removed and stirring is continued for an additional 10 minutes. A solution of 38.0 g. (36.5 ml., 0.25 mole) of orcinol dimethyl ether in 100 ml. of dry dimethylformamide (Note 6) is added in one lot, and the mixture is refluxed under an atmosphere of dry nitrogen for 3 hours (Notes 8 and 9), The mixture 

Technical acetone containing about 1% water is quite satisfactory. 

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Orcinol, dimethyl ether, 53, 90 ORCINOL MONOMETHYL ETHER, 53,... 

Orcinol dimethyl ether Orcinol monomethyl ether >240 153,328... 

Previous preparations of orcinol monomethyl ether have been effected by partial methylation of oricinol with methyl iodide and potassium hydroxide3 or sodium ethoxide,4 or with dimethyl sulfate and sodium hydroxide.5 These procedures required tedious purification stages and the pure monomethyl ether was obtained in 37 % yield at best.5... 

Octene-l-al, 38,62 2-Octenes, 303 2-Octylamine, 554 4-Octyne, 96 2-Octyne-l-ol, 62 4-Octyne-3-one, 96 Olefin inversion, 303-304 Olefin methathesis, 570 Orcinol dimethyl ether, 465 Orcinol monomethyl ether, 465 Osmium tetroxide, 31,575,576 Osmium tetroxide-Potassium chlorate, 361... 

Verticicladiella spp. 5-Alkylresorcinol Orcinol monomethyl ether and C2-C6 homologues - 71 Canada... 

CAS 3209-13-0 EINECS/ELINCS 221-716-1 Synonyms 3-Hydroxy-5-methyltoluene 3-Methoxy-5-methylphenol Orcinol monomethyl ether... 

Orchis mascula Orchis mascula extract. See Orchid (Orchis mascula) extract Orcinol monomethyl ether Orclnyl 3. SeeS-Methoxy-m-cresol Oreo Antifoam AF. See Silicone Oreo Binder LF-X. See Aery I i c res i n Oreo Dye Carrier B. See Butyl benzoate Oreo Low Crock T-550. See Acrylic resin Orcoset Resin CN. See Polyvinyl acetate... 

Preparation by reaction of acetonitrile on orcinol monomethyl ether (Hoesch reaction) (32%) [2301]. 

Obtained (poor yield) by condensation of phenylacetonitrile with orcinol monomethyl ether (7%) (Hoesch reaction) [5336]. 

Also obtained by reaction of propionic anhydride with orcinol monomethyl ether in the presence of concentrated sulfuric acid at 130° [6744]. m.p. 75° [6744],... 

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