Melting points were determined on a Reichert microscope with Kofler heating and are uncorrected. NMR spectra were recorded on a Varían A-60 instrument using CDC13 or D20 as solvents and Me4Si or sodium 3-(trimethylsilyl) propanesulfonate (TMSPS) as internal standards. Elemental analyses indicated were within ą0. 4% of the theoretical values. All o-dihydroxy-arenes were from commercial sources except for 2, 3-dihydroxy-5, 6, 7, 8-tetrahydronaphthalene which was prepared from veratrole according to Haworth and Mavin; 10 the final step, namely, demethylation of the methoxy groups, was accomplished in 96% yield by treatment with BBr3 in CH2C12 according to McOmie et al. 11 l, l'-(3-Methylphenylene-l, 2-dioxy) bis (3-chloro-2-propanol)(2a). A solution of 12.4 g (0.1 mol) of 3-methylcatechol, 37.0 g (0.4 mol) of epichlorohydrin and 0.4 mL of 10 N NaOH was stirred under N2 at 40 C for 48 h. After evaporation of the epi-chlorohydrin in vacuo at 40 C, the residual oil was taken up in CHC13, washed twice, and concentrated. Molecular distillation yielded 21.3 g of impure 2a. l, l'-(3-Methylphenylene-l, 2-dioxy) bis (3-isopropyl-amino-2-propanoI)(2). A solution of 13.1 g of impure 2a, 14.8 g (0.25 mol) of i-PrNH2, and 15.0 mL of C6H6 was heated in a Carius tube at 80 C for 8 h. After concentration, the product was taken up in 4 N AcOH and extracted carefully with CHClg. The amino ether was liberated with 2 N NaOH, taken up in

CHClg, washed, and concentrated to give 0.0252 mol of 2 in a purity of 99.6%(potentiometric titration): yield, as calculated with reference to 3-methylcatechol, 43%. The compound was taken up in anhydrous Ét20 and treated with the calculated amount of ethereal HC1 solution to afford the dihydrochloride salt. On TLC (silica gel GF254, 20 vol% Me2CO in CHClg) of the original CHClg extract only one spot appeared. GLC (20% SE-30 on Chromosorb W 60-80) confirmed12 it to consist of a mixture of 2-hydroxymethyl-5-and-8-methylbenzodioxane. Single molecular distillation gave 0.0206 mol: n20D 1.5510 (lit. 12 n2sD 1.5488 and 1.5510 for the 5-methyl and 8-methyl isomer, re-spectively); total yield of amino ether and benzodioxanes, 0.0458 mol. Anal.(C10H12O3) C, H.