ChemicalBook CAS DataBase List METHYL 10-HYDROXYDECANOATE

METHYL 10-HYDROXYDECANOATE synthesis

12synthesis methods

Product Name:METHYL 10-HYDROXYDECANOATE
CAS Number:2640-94-0
Molecular formula:C11H22O3
Molecular Weight:202.29

111-81-9 Synthesis

111-81-9
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2640-94-0
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$129.00/10g

Yield: 91.3%

Reaction Conditions:

Stage #1:Methyl 10-undecenoate with ozone in methanol;dichloromethane at -78; for 1 h;
Stage #2: with sodium tetrahydroborate in methanol;dichloromethane at 20; for 8 h;
Stage #3: with water;ammonium chloride

Steps:

7
EXAMPLE 7; Synthesis of Alcohol (24); Methyl 10-undecenoate (1.50 g, 7.56 mmol) in dichloromethane and methanol (45.4 mL, 1:1) was stirred at -78° C. for 1 hour while introducing ozone thereto. Nitrogen gas was introduced thereto for 5 minutes to remove ozone and then thereto was added sodium borohydride (429 mg, 11.4 mmol). The mixture was stirred for 8 hours while gradually rising to room temperature. To the reaction mixture was added an aqueous saturated ammonium chloride solution and after neutralizing, the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate and the organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure and the residue was purified with silica gel column chromatography (from 25% to 33% ethyl acetate in hexane) to give Alcohol (24) (1.40g, 91.3%). IR (NaCl neat): 3385.38, 1739.95, 1437.10, 1172.83, 1057.09 cm^-1¹H NMR (CDCl₃, 400 MHz) δ: 3.67 (s, 3H), 3.63 (t, J=6.8 Hz, 2H), 2.30 (t, J=7.6 Hz, 2H), 1.93 (brs, 1H), 1.64 (m, 2H), 1.55 (m, 2H), 1.30 (m, 10H); ¹³C NMR (CDCl₃, 100 MHz) δ: 174.3, 62.8, 51.4, 34.0, 32.7, 29.3, 29.3, 29.1, 29.0, 25.6, 24.8.

References:

Katsumura, Shigeo;Hakogi, Toshikazu;Shigenari, Toshihiko US2005/182265, 2005, A1 Location in patent:Page/Page column 10