3.7- Dimethyl-1,7-octanedio

Dimethyl octanedioate (dimethyl suberate), 71.2 g (0.352 mol), 1,4-butanediol (5% excess 0.370 mol, 33.3 g), and 0.02 g of tetraisopropoxytitanium (0.025% of final polyester mass) are placed in a three-necked round-bottomed flask fitted with a mechanical stirrer. The medium is slowly heated to 150°C within 4 h under nitrogen atmosphere while methanol is distilled off. Vacuum is then slowly applied and the reaction continued at 0.01 mbar and 150°C for 48 h. The resulting polyester is cooled down, dissolved in chloroform (50 g polyester/200 mL chloroform), and slowly added to a 10-fold volume of methanol under high-speed agitation (1000 rpm). The precipitated polyester is filtered off and dried at 30°C under vacuum (0.1 mbar). 

Cyclooctene gives dimethyl octanedioate under these conditions. 

Cyclooctene gives dimethyl octanedioate under these conditions. Scheme 12.18 illustrates some cases in which ozonolysis reactions have been used in the course of synthesis. 

Figure 11.1 Py/methylation GC/MS chromatograms of lead white pigmented linseed oil paint after 610 °C Curie point pyrolysis assisted with on line methylation using 2.5% methanolic TMAH (the sample and TMAH solution was applied onto a rotating Curie point wire pyrolysis time 6 s, interface 180°C). 1, heptenoic acid, methyl ester 2, heptanoic acid, methyl ester 3, butenedioic acid, dimethyl ester 4, butanedioic acid, dimethyl ester 5, octenoic acid, methyl ester 6, octanoic acid, methyl ester 7, pentenedioic acid, dimethyl ester 8, pentanedioic acid, dimethyl ester 9, nonanoic acid, methyl ester 10, hexanedioic acid, dimethyl ester 11, decanoic acid, methyl ester 12, heptanedioic acid, dimethyl ester 13, octanedioic acid, dimethyl ester 14, 1,2 benzenedicarboxylic acid, dimethyl ester 15, a methyl octanedioic acid, dimethyl ester 16, nonanedioic acid, dimethyl ester 17, a methoxy octanedioic acid, dimethyl ester 18, a methyl nonanedioic acid, dimethyl ester 19, a,a dimethyl nonenedioic acid, dimethyl ester 20a, a methyl nonenedioic acid, dimethyl ester 20b, a,a dimethyl nonanedioic acid, dimethyl ester 21, decanedioic acid, dimethyl ester 22, a methoxy nonanedioic acid, dimethyl ester 23, a methyl decan edioic acid, dimethyl ester 24, undecanedioic acid, dimethyl ester 25, a methoxy decan edioic acid, dimethyl ester 26, pentadecanoic acid, methyl ester 27, dodecanedioic acid, dimethyl ester 28, hexadecanoic acid, methyl ester 29, heptadecanoic acid, methyl ester 30, octadecanoic acid, methyl ester 31,8 methoxy 9 octadecenoic acid, methyl ester 32, 11 methoxy 9 octadecenoic acid, methyl ester 33, 9 methoxy 10 octadecenoic acid and 10 methoxy 8 octadecenoic acid 34, 9 oxo octadecanoic acid, 10 oxo octadecanoic acid 35, 9 epoxy octadecanoic acid 36, eicosanoic acid, methyl ester 37, 9,10 dimethoxy octadecanoic acid, methyl ester 38, docosanoic acid, methyl ester. Reprinted from J. Anal. Appl. Pyrol., 61, 1 2, van den Berg and Boon, 19, Copyright 2001, with permission from Elsevier...

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