Synthesis of diethyl benzylpropanedioate

Preparation of diethyl benzylpropanedioate

Alternative Names: Benzylmalonic acid diethyl ester; Diethyl 2-benzylmalonate; Diethyl 2-benzylpropanedioate; Malonic acid, benzyl-, diethyl ester;

Preparation of diethyl benzylpropanedioate

Preparation of diethyl benzylpropanedioate

7.2 g sodium are dissolved in 150 ml absolute ethyl alcohol, then 50 g diethyl malonate and 43 g pure benzyl chloride are added. In a few minutes’ time much heat is evolved, and the clear solution deposits a precipitate of sodium chloride; after 10 minutes the alcohol is evaporated off on the water-bath or vacuo without previous filtration. The reaction of the liquid is at the end only weakly alkaline. The residue is treated with water to dissolve the sodium chloride, and the oil which separates is extracted with ether. The ethereal solution is dried with potassium carbonate, or with anhydrous sodium sulfate; the ether is distilled off, and the residue is fractionated under diminished pressure. At 11 mm pressure the diethyl benzylpropanedioate (benzylmalonic ester) passes over for the most part at 166-169° C as a colorless mobile oil. The distillate is collected up to 175° C. The yield of diethyl benzylpropanedioate is 45-50 g. A second fractionation yields 40-45 g of a product, which boils at 166-168° C. The ester boils under 15 mm pressure at 173° C, under 20 mm at 183° C, and under 25 mm at 188° C.

Introduction to the preparation of organic compounds, E. Fisher, 78-79, 1909

IUPAC Name

diethyl 2-benzylpropanedioate

InChI

InChI=1S/C14H18O4/c1-3-17-13(15)12(14(16)18-4-2)10-11-8-6-5-7-9-11/h5-9,12H,3-4,10H2,1-2H3

InChI Key

ICZLTZWATFXDLP-UHFFFAOYSA-N

Canonical SMILES

CCOC(=O)C(CC1=CC=CC=C1)C(=O)OCC

Depositor-Supplied Synonyms

Diethyl benzylmalonate, 607-81-8, Benzylmalonic acid diethyl ester, Diethyl 2-benzylmalonate, diethyl 2-benzylpropanedioate, Malonic acid, benzyl-, diethyl ester, Propanedioic acid, (phenylmethyl)-, diethyl ester, Malonic acid, 2-benzyl-, diethyl ester, ICZLTZWATFXDLP-UHFFFAOYSA-N, 1,3-diethyl 2-benzylpropanedioate, diethyl (phenylmethyl)propanedioate, NSC 8720, EINECS 210-142-7, NSC 41169, NSC631631, SBB042558, AI3-01359, Propanedioic acid, 2-(phenylmethyl)-, 1,3-diethyl ester, diethyl 2-benzylpropane-1,3-dioate, 581796-75-0, diethyl benzyl malonate, ACMC-209mly, diethyl benzylpropanedioate, DIETHYLBENZYLMALONATE, AC1L2B3G, AC1Q63TW, Diethyl 2-benzylmalonate #, UNII-40Y0X0XN6P, KSC191A7F, SCHEMBL165382, 135542_ALDRICH, 40Y0X0XN6P, 13532_FLUKA, NSC8720, MolPort-000-861-074, 2-benzylmalonic acid diethyl ester, NSC-8720, NSC41169, ANW-33572, AR-1I4627, NSC-41169, STL264259, ZINC01648200, AKOS000120927, MCULE-9234747508, NSC-631631, RTR-037259, TRA0083938, AJ-28720, AK-48383, AN-46390, BR-48383, CJ-05921, CJ-26614, M280, OR025300, OR288986, KB-251468, LS-184889, TR-037259, AM20040831, B0423, FT-0622854, ST24030350, ST50406622, M-7270, S01-0398, 3B3-027232

Removed Synonyms

Malonic acid, diethyl ester, Propanedioic acid, diethyl ester, CID69090, 62554-36-3

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