M etherdiethyl ether, affording the crude compounds 3 and 4, respectively.(E)-3,7-dimethyl-8-oxoocta-1,6-dien-3-yl-acetate (four), 8-oxolinalyl AcetateFollowing GP1,

M etherdiethyl ether, affording the crude compounds 3 and 4, respectively.(E)-3,7-dimethyl-8-oxoocta-1,6-dien-3-yl-acetate (four), 8-oxolinalyl AcetateFollowing GP1, from 2 (5 g, 25 mmol) and selenium dioxide (two.7 g, 25 mmol) in 15 ml Ethyl phenylacetate Formula dioxaneethanol 9:1 (vv), compound 4 was prepared. Flash chromatographic purification with petroleum etherdiethyl ether three:two(vv) yielded 1.4 g (29 ) of four as orange oil.1 H NMR (600 MHz, CHLOROFORM-d) ppm 9.39 (1 H, s), 6.44.50 (1 H, m), 5.96 (1 H, dd, J = 17.56, 11.14 Hz), five.15.26 (two H, m), 2.37 (two H, q, J = 7.93 Hz), two.06.12 (1 H, m), two.02 (3 H, s), 1.87.95 (1 H, m), 1.74 (3 H, s), 1.59 (three H, s).13 C NMR (151 MHz, CHLOROFORM-d) ppm 195.1, 169.9, 153.7, 141.1, 139.5, 113.eight, 82.3, 38.1, 23.79, 23.79, 22.1, 9.12. MS (EI) mz(rel.int.): 210 [M+ ] (1), 150(18.38), 135(14), 121(19), 107(18.05), 93(26), 82(41), 71(46), 55(29), 43(one hundred).(E)-3,7-dimethyl-8-oxoocta-1,6-dien-3-ol (3), 8-oxolinaloolFollowing GP1, from 1 (four.eight g, 31.1 mmol) and selenium dioxide (three.four g, 30.four mmol) in 30 ml dioxaneethanol 9:1 (vv), compound 3 was prepared. Flash chromatographic purification with petroleum etherdiethyl ether 1:four (vv) yielded 1.four g (29 ) of three as orange oil.1 H NMR (600 MHz, CHLOROFORM-d) ppm 9.38 (1 H, s), 6.42.56 (1 H, m), five.92 (1 H, dd, J = 17.26, 10.67 Hz), five.25 (1 H, dd, J = 17.26, 0.91 Hz), 5.11 (1 H, dd, J = ten.90, 0.91 Hz), two.35.45 (2 H, m), 1.74 (3 H, s), 1.61.71 (2 H, m), 1.31.35 (three H, m).13 C NMR (91 MHz, CHLOROFORMd) ppm 195.two., 154.six, 144.three, 139.two, 112.4, 72.9, 40.three, 28.1, 23.eight, 9.1.MS (EI) mz(rel.int.): 168 [M+ ] (1), 98(15), 87(27), 82(24), 71(one hundred), 55(33), 43(58), 41(23).Procedure 2 (E)-8-hydroxy-3,7-dimethylocta-1,6-dien-3-yl-acetate (five), 8-hydroxylinalyl AcetateCompound four (800 mg, three.81 mmol) was dissolved in dry methanol (40 ml) and sodium Acs pubs hsp Inhibitors MedChemExpress borohydride (NaBH4 ; 1.8 g, four.72 mmol) was added (Liu et al., 2003; Scheme two). The solution was allowed to stir at -10 C. Immediately after 1 h, water was added as well as the reaction mixture was extracted with dichloromethane (DCM). The organic layer was dried more than sodium sulfate. Immediately after removal on the solvent, the residue was subjected to flash chromatography eluted with petroleum etherdiethyl ether two:three (vv) and yielded 626 mg (77 ) of five as light yellow oil.1 H NMR (360 MHz, CHLOROFORM-d) ppm five.97 (1 H, dd, J = 17.48, 10.90 Hz),SCHEME 2 | Synthetic pathways for the synthesis of linalool and linalyl acetate oxygenated derivatives following procedures 1-4.Frontiers in Chemistry | www.frontiersin.orgOctober 2015 | Volume three | ArticleElsharif et al.Structure-odor relationships of linalool and derivatives5.36.43 (1 H, m), 5.15 (2 H, dd, J = 17.48, 11.13 Hz), three.99 (2 H, d, J = five.45 Hz), 2.03.09 (two H, m), two.01 (three H, s), 1.75.96 (two H, m), 1.66 (three H, s), 1.55 (three H, s). 13 C NMR (91 MHz, CHLOROFORM-d) ppm 169.9, 141.7, 135.two, 125.4, 113.three, 82.8, 68.8, 39.4, 23.7, 22.2, 21.9, 13.six. MS (EI) mz(rel.int.): 211 [M+ -1] (1), 134(7), 119(27), 93(46), 79(35), 67(30), 55(24), 43(one hundred).182 [M+ -2] (1), 151(4), 138(7), 121(15), 111(14), 103(16), 95(16), 82(11), 71(100), 67(18), 55(24).(E)-6-acetoxy-2,6-dimethylocta-2,7-dienoic-acid (8), 8-carboxylinalyl AcetateFollowing GP4, compound four (0.3 gm, 1.24 mmol) was dissolved in 25 ml tert-butyl alcohol and 6 ml 2-methyl-2-butene. A answer of sodium chlorite (1.08 gm, 11.four mmol) and sodium dihydrogenphosphate (1.05 gm, 8.55 mmol) in 10 ml water was added dropwise more than a 10 min period, compound 8 was ready. Flash chromatographic purification with ethyl acetatemetha.