| Identification | Back Directory | [Name]
Dimethyl 2-(2-methoxyphenoxy)malonate | [CAS]
150726-89-9 | [Synonyms]
2-MethoxyphenoxyMalonate
DIMETHYL (2-METHOXYPHENOXY)MALONATE
Dimethyl (o-Methoxyphenoxy)malonate
Dimethyl-2-(2-methoxyphenoxy)malonate
1,3-diMethyl 2-(2-Methoxyphenoxy)propanedioate
2-(2-Methoxyphenoxy)malonic acid dimethyl ester
(2-Methoxyphenoxy)-propanedioic Acid Dimethyl Ester | [EINECS(EC#)]
604-747-9 | [Molecular Formula]
C12H14O6 | [MDL Number]
MFCD06797652 | [MOL File]
150726-89-9.mol | [Molecular Weight]
254.24 |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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 |
| Hazard Information | Back Directory | [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 |
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