[CH2:1]([O:3][CH:4]([CH2:14][O:15][CH2:16][CH3:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:18][S:19][CH2:20][CH2:21]Br>[OH-].[K+].C(O)C>[CH3:18][S:19][CH2:20][CH2:21][O:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH:4]([O:3][CH2:1][CH3:2])[CH2:14][O:15][CH2:16][CH3:17])=[CH:8][CH:9]=1A 2.40 g quantity of 4-(2,3-diethoxypropoxy)phenol was dissolved in 0.56 g of potassium hydroxide and 10 ml of 90% ethanol. To the solution was added 1.55 g of 2-methylmercaptoethyl bromide. The mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated and the residue was extracted with chloroform. The chloroform layer was washed with water, dewatered with Glauber's salt and concentrated. The residue was distilled at reduced pressure, giving 2.95 g of 2-{4-(2,3-diethoxypropoxy)phenoxy}ethyl methyl sulfide in 93.9% yield, b.p. 176° to 177° C./l to 2 mmHg.
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