ChemicalBook CAS DataBase List METHYL 3-HYDROXYDECANOATE

METHYL 3-HYDROXYDECANOATE synthesis

7synthesis methods

Product Name:METHYL 3-HYDROXYDECANOATE
CAS Number:62675-82-5
Molecular formula:C11H22O3
Molecular Weight:202.29

124-13-0
353 suppliers
$7.00/25g

96-32-2
335 suppliers
$15.00/5g

62675-82-5
38 suppliers
$25.00/1mg

Yield:62675-82-5 92%

Reaction Conditions:

with zinc in tetrahydrofuran at 66; for 0.0166667 h;Reformatsky Reaction;

Steps:

Reformatsky Reaction; General Procedure

General procedure: THF (200 mL) was added to an oven-dried 500 mL round-bottomedflask equipped with a condenser 30 cm in length and left open to theatmosphere. The THF was used directly as purchased without any furtherdrying or purification. The solvent was then rapidly stirred usinga magnetic stir bar and brought to reflux (66 °C) on a sand bath. Thecondenser was then temporarily raised and 6.5 g (0.1 mol, 2 equiv) ofZn granules were added to the hot solvent. This was followed by therapid addition of the aldehyde (0.1 mol) and the bromoacetate (as eitherthe methyl or ethyl ester) (0.2 mol, 2 equiv) into the reactionmixture. The condenser was immediately reattached to the roundbottomed flask at which point rapid boiling occurred. The reactionwas allowed to rapidly reflux for 1 min at which point the reactionvessel was removed from heat and allowed to cool to r.t. with stirring. The reaction was observed to be complete by TLC (eluent: hexanes-EtOAc, 80:20) within 20 min for all substrates. Excess THF was removed under vacuum and the resultant brown oil was dissolved inhexanes and quenched with H2O to form a yellow precipitate. Themixture was filtered and the hexane layer was washed with H2O (100mL), aq 1 M HCl (2 × 50 mL), H2O (100 mL) and brine (50 mL), anddried (Na2SO4). Removal of hexanes under vacuum furnished the products 1-8 in yields ranging from 86 to 95% (Table 1).

References:

Sailer, Miloslav;Dubicki, Krystyn I.;Sorensen, John L. [Synthesis,2015,vol. 47,# 1,art. no. SS-2014-M0434-OP,p. 79 - 82]