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(S)-(-)-Dimethyl malate

(S)-(-)-Dimethyl malate structure

CAS No:
617-55-0
Formula:
C6H10O5
Chemical Name:
(S)-(-)-Dimethyl malate
Synonyms:
Butanedioic acid,2-hydroxy-,1,4-dimethyl ester,(2S)-;Malic acid,dimethyl ester,L-;Butanedioic acid,hydroxy-,dimethyl ester,(S)-;Butanedioic acid,hydroxy-,dimethyl ester,(2S)-;(S)-(-)-Dimethyl malate;Dimethyl (S)-malate;(S)-Malic acid dimethyl ester;(-)-Dimethyl malate;Dimethyl L-malate;L-Malic acid dimethyl ester;Dimethyl (S)-2-hydroxybutanedioate;Dimethyl (S)-(-)-2-hydroxysuccinate;(2S)-Hydroxysuccinic acid dimethyl ester;Dimethyl (2S)-2-hydroxysuccinate;(S)-Dimethyl 2-hydroxysuccinate;1,4-Dimethyl (2S)-2-hydroxybutanedioate;113240-52-1
Categories:
Organic Chemistry > Coordination Complexes

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Description

Colourless Oil

(S)-(-)-Dimethyl malate Basic Attributes

Molecular Weight：

162.14

Exact Mass：

162.14

EC Number：

432-310-0

HScode：

2918199090

Characteristics

PSA：

72.8

XLogP3：

-0.7

Density：

1.0079 g/cm³ @ Temp: 25.00 °C

Boiling Point：

249.6°C at 760 mmHg

Flash Point：

100.1±15.3 °C

Refractive Index：

1.440

Safety Information

Transport codes：

UN 1993C 3 / PGIII

wgk germany：

hazard class code：

R36/37/38

safety instructions：

S26-S36

Marks：

Precautionary statement(s)：

P210-P280-P305 + P351 + P338 + P310-P333 + P313-P403 + P235

Hazard Statements：

H226-H317-H318

(S)-(-)-Dimethyl malate Use and Manufacturing

Thionyl chloride (117 g, 0.98 mol) was added to the solution of L-malic acid (59.9 g, 0.45 mol) in methanol (400 mL) in ice-water bath. The resulting reaction mixture was stirred overnight at room temperature (rt, 25 °C) after the completion of the addition. The reaction was monitored with TLC (EtOAc:MeOH =10:1). The solvent was removed in vacuo. Saturated NaHCOTo a 2 L flask charged with stir bar andanhydrous methanol (500 mL) was added acetyl chloride (22.4 mL, 315 mmol, 0.6equiv) dropwise. The resultant solution was stirred for 10 min at rt, then (S)-malic acid(70.55 g, 526 mmol) was added. The reaction was stirred overnight at rt, thenconcentrated in vacuo. Silica gel chromatography (96:4 CH2Cl2/MeOH) afforded the titlecompound as a pale yellow oil (80.57 g, 94percent), with spectroscopic data in agreementwith literature values.15Acetyl chloride (8.21 mL, 116 mmol) was added to methanol (150 mL) at room temperature followed after 10 min by (S)-malic acid (25 g, 186 mmol). The solution was stirred at room temperature for 18 h before the volatile components were evaporated under reduced pressure. The resultant residue was purified by flash column chromatography using CHIn a reaction vessel23.6 g (0.2 mol)L-malic acid, And methanol was added40 ml, To dissolve, Concentrated sulfuric acid was then added4ml, After heating under reflux for 3 hours, Cooled to room temperature, The reaction solution was poured into water, Fully stirred, The residue was diluted with dichloromethane (50 ml * 3)extraction, The organic phases were combined, Washed, Dried over anhydrous sodium sulfate, stress reliever, After recovery of the solvent by distillation, To give dimethyl L-malate as a white solid18.8 g, Yield64.8percent.

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