Monoacetate monomethyl ether

Ethylene glycol monoacetate, hi 16 Ethylene glycol monobutyl ether, b410 Ethylene glycol monoethyl ether, e34 Ethylene glycol monomethyl ether, m65 Ethylene glycol monomethyl ether acetate, m68 Ethylene iodide, d403 Ethylene iodohydrin, i35... 

The tetrahydro cannabinols form acyl derivatives, such as the monoacetates, and ether-derivatives such as the monomethyl ether, with specific rotations corresponding to the rotation of the tetrahydro cannabinol from which each may be formed. 

Both 10-hydroxy- (20) and lO-methoxycanthin-6-one (21) have been isolated from the wood of 5. multiflora (42), and 20 has also been isolated from the root of Eurycoma longifolia (43). The UV spectrum of 20 shows a large bathochromic shift (76 nm) on alkali addition. Both the UV and IR spectra of 20 resemble those of 18. Acetylation and methylation of 20 produce the monoacetate and monomethyl ether, respectively. In the H-NMR spectrum of 20, two isolated pairs of vicinal protons in rings C and D and 1, 2, 4-trisubstituted aromatic protons are observed. From these observations Arisawa et al. (42) concluded that the hydroxyl function should associate with position 9 or 10. The position was fixed by the interlocking evidence, and structure 20 was determined. There was an increase in the molecular ion of 14 mass units in the mass spectrum of 21 as compared to 20 and the appearance of a new signal (8 3.91, 3H, s)... 

Monoacetals of quinones are accessible by T1(N02)3 oxidation of hy-droqulnone monomethyl ethers. The unprotected carbonyl group can be condensed with anions to afford products which give substituted phenylacetic acid derivatives on aromatization. 

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