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ChemicalBook CAS DataBase List 20-(tert-Butoxy)-20-oxoicosanoic acid
683239-16-9

20-(tert-Butoxy)-20-oxoicosanoic acid synthesis

3synthesis methods
20-(tert-Butoxy)-20-oxoicocosanoic acid can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly in laboratory research and development.  It was synthesized from eicosanedioic acid and N,N dimethylformamide di-tert-butylacetal  by stirring in  toluene for 30 min at 95° C.
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Yield:683239-16-9 722 mg (21%)

Reaction Conditions:

in dichloromethane;toluene

Steps:

2 Building Block 1 Eicosanedioic Acid Mono-Tert-Butyl Ester:
Building Block 1 Eicosanedioic Acid Mono-Tert-Butyl Ester: To eicosanedioic acid (3 g, 8.76 mmol) was added toluene (25 mL) and N,N dimethylformamide di-tert-butylacetal (2.1 mL, 8.76 mmol). The mixture is heated to 95° C. for 30 minutes, the mixtures is filtered and evaporated to an oil, which is redisolved in dichloromethane and washed with water. The organic phase is dried and evaporated to give 722 mg (21%) of the title compound, which was subsequently used without any further purification. 1H NMR (CDCl3): δ10.90 (br s, 1H), 2.35 (t, 2H), 20 (t, 2H), 1.60 (m, 4H), 1.45 (s, 9H); 1.40-1.20 (m, 28H)

References:

Thim, Lars;Bang, Susanne;Schlein, Morten;Kaarsholm, Niels Christian;Engelund, Dorthe Kot;Nielsen, Anette Sams;Johansen, Nils Langeland;Madsen, Kjeld;Zundel, Magali;Thygesen, Peter US2004/122210, 2004, A1

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