ChemicalBook CAS DataBase List D-(+)-MALIC ACID DIMETHYL ESTER

D-(+)-MALIC ACID DIMETHYL ESTER synthesis

5synthesis methods

Product Name:D-(+)-MALIC ACID DIMETHYL ESTER
CAS Number:70681-41-3
Molecular formula:C6H10O5
Molecular Weight:162.14

67-56-1 Synthesis

67-56-1
736 suppliers
$7.29/5ml-f

636-61-3 Synthesis

636-61-3
370 suppliers
$6.00/5g

70681-41-3
118 suppliers
$40.00/5g

Yield:70681-41-3 99%

Reaction Conditions:

with thionyl chloride at 0 - 20;Inert atmosphere;

Steps:

(R)-Dimethyl 2-hydroxysuccinate (5)
SOCl₂(2.40 mL) was added dropwise to a solution of (R)-malic acid 4 (2.0024 g, 15 mmol) in MeOH (20 mL) at 0^oC. The solution was stirred at room temperature for 24 hours then concentrated under reduced pressure. Flash chromatography (1:1 EtOAc:Pet ether) gave 5 (2.4034 g, 99%) as a light yellow oil, with spectral data in accordance with the literature [6, 7]. R_f (1:1 EtOAc:Pet ether): 0.30. ¹H NMR (500 MHz, CDCl₃) ppm 4.52 (q, J = 5.5 Hz, 1H, H2), 3.82 (s, 3H, OCH₃), 3.72 (s, 3H, OCH₃), 2.95-2.74 (m, 2H, H3). ¹³C NMR (126 MHz, CDCl₃) d ppm 173.9, 171.2, 67.4, 53.1, 52.2, 38.6. HRMS (ESI): Calcd. for C₆H₁₀NaO₅ [M+Na]⁺: 185.0420; found: 185.0427.

References:

Tran, David;Pietersma, Amy L.;Schofield, Linley R.;Rost, Matthias;Jameson, Geoffrey B.;Parker, Emily J. [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 22,p. 6838 - 6841] Location in patent:supporting information; experimental part

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636-61-3 Synthesis

636-61-3
370 suppliers
$6.00/5g