METHYL 3-OXOTETRADECANOATE Property

Melting point:

29-30°C

Boiling point:

137-139 °C(Press: 0.9 Torr)

Density 

0.926±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Solid

pka

10.65±0.46(Predicted)

color 

Light Yellow to Yellow

LogP

5.500 (est)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

METHYL 3-OXOTETRADECANOATE Chemical Properties,Usage,Production

Synthesis

The carboxylic acid (13.8 g, 69 mmol, 1.0 equivalents) was dissolved in dry THF under an inert atmosphere and cooled to 0 ºC. CDI (13.4 g, 83 mmol, 1.2 equivalents) was then added in small portions over several minutes. After 10 min, the reaction was allowed to warm slowly to room temperature and was then stirred for 1 h. In a separate flflask, monomethyl malonate (9.8g, 83 mmol, 1.2 equivalents) was dissolved in THF under an inert atmosphere and cooled to −78 ºC. To this solution was added dibutylmagnesium (1.0 M in heptane, 0.6 equivalents). A white solid formed instantly on addition of the base. After 10 min, the reaction was warmed to room temperature and stirred for 1 h. The acylimidazole was then added by cannula to the flflask containing the magnesium salt. The resulting slurry was stirred for  3 days. The reaction mixture was then concentrated on a rotary evaporator and the residue redissolved in EtOAc. The resulting solution was washed with 1.2 M HCl, saturated aqueous NaHCO3, and brine. The organic phase was dried over sodium sulfate, fifiltered, concentrated, and the residue purifified by flflash chromatography (7:1 hexanes:EtOAc) to give the β-keto ester (14.7g, 83%).

Reference: Durham, T. B.; Miller, M. J. J. Org. Chem. 2003, 68, 27–34.

Chemical Properties

Yellow Crystalline Solid

Uses

Methyl 3-Oxotetradecanoate (cas# 22348-97-6) is a compound useful in organic synthesis.