Dimethyl 2-(2-methoxyphenoxy)malonate Chemical Properties

Boiling point:

320.5±27.0 °C(Predicted)

Density 

1.206±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Dichloromethane, Methanol

form 

Solid

pka

12.17±0.59(Predicted)

color 

White

InChI

InChI=1S/C12H14O6/c1-15-8-6-4-5-7-9(8)18-10(11(13)16-2)12(14)17-3/h4-7,10H,1-3H3

InChIKey

SBUXKADXTZOBJV-UHFFFAOYSA-N

SMILES

C(OC)(=O)C(OC1=CC=CC=C1OC)C(OC)=O

Dimethyl 2-(2-methoxyphenoxy)malonate Usage And Synthesis

Chemical Properties

White Solid

Uses

Dimethyl 2-Methoxyphenoxymalonate (cas# 150726-89-9) is a compound useful in organic synthesis.

Synthesis

Sodium methanol solution (2.3 g Na, 0.10 mol, 1.0 eq., dissolved in 75 ml of methanol) was slowly added dropwise to a stirred mixture of guaiacol (12.5 g, 0.100 mol, 1.0 eq.) and dimethyl 2-chloromalonate (19.0 g, 0.114 mol, 1.14 eq.). The reaction mixture was stirred at 45 °C for 1 hour. After completion of the reaction, the volatiles were evaporated by rotary evaporator. The residue was dissolved in toluene and washed sequentially with deionized water and 1% aqueous sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 20.0 g (78.7% yield) of dimethyl 2-(2-methoxyphenoxy)malonate as a viscous oil. The product characterization data were as follows: boiling point 131 °C (literature value 128 °C); 1H NMR (CDCl3) δ 7.12-7.00 (m, 2H), 6.98-6.90 (m, 1H), 6.90-6.82 (m, 1H), 5.27 (s, 1H), 3.85 (s, 3H), 3.84 (s, 6H); 13C NMR ( CDCl3) δ 166.2 (2C), 150.4,146.0,124.4,120.8,119.0,112.5,78.4,55.8,53.0 (2C); HRMS calculated value of C12H14O6 255.0869 (M+H+), measured value 255.0870 (M+H+).

References

[1] European Journal of Medicinal Chemistry, 2016, vol. 121, p. 658 - 670
[2] Organic Preparations and Procedures International, 2016, vol. 48, # 6, p. 481 - 491
[3] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 4, p. 897 - 907
[4] Patent: US5292740, 1994, A
[5] Patent: WO2011/24056, 2011, A2. Location in patent: Page/Page column 19

Dimethyl 2-(2-methoxyphenoxy)malonate(150726-89-9)Related Product Information

• (Trifluoromethoxy)benzene
• Dimethyl sulfoxide
• Dimethyl sulfate
• Malonic acid
• ETHANE
• 4-Methoxybenzoic acid
• Dimethyl methylmalonate
• 4-Methoxybenzoyl chloride
• Dimethyl malonate
• N,N-Dimethylformamide
• Malononitrile
• p-Anisaldehyde
• Diethyl malonate
• Dimethyl carbonate
• Dimethyl fluoromalonate
• 4-Methoxybenzyl alcohol
• Dimethyl isobutylmalonate
• 2,2-DIMETHYL-MALONIC ACID DIMETHYL ESTER