3-Hydroxyoctadecanoic acid methyl ester synthesis
- Product Name:3-Hydroxyoctadecanoic acid methyl ester
- CAS Number:2420-36-2
- Molecular formula:C19H38O3
- Molecular Weight:314.5
Yield:2420-36-2 98%
Reaction Conditions:
with sodium tetrahydroborate for 12 h;
Steps:
Methyl 3-hydroxyoctadecanoate (17)
Ketoester 16 (750 mg, 2.3 mmol, 1 eq) was dissolved in methanol (2 mL) and NaBH4(44 mg, 1.15 mmol, 0.5 eq) was slowly added while stirring. The reaction mixture wasstirred for 12 h and then concentrated in vacuo. The residue was mixed with water andextracted three times with TBME. The combined organic layers were washed with brineand dried with MgSO4. The solvent was removed under vacuum and the product 17was obtained in quantitative yield (723 mg, 2.3 mmol) as a yellowish, waxy solid.During the reaction transesterification to the methyl ester was observed.
References:
Elias, Marianne;Mann, Florian;McClure, Melanie;Schulz, Stefan;Silva, Lisa de;Szczerbowski, Daiane [Beilstein Journal of Organic Chemistry,2020,vol. 16,p. 2776 - 2786] Location in patent:supporting information
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