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ChemicalBook CAS DataBase List 3,3-DIETHOXYPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER

3,3-DIETHOXYPROPANE-1,1-DICARBOXYLIC ACID DIETHYL ESTER synthesis

2synthesis methods
-

Yield: 78%

Reaction Conditions:

with potassium tert-butylate in N,N-dimethyl-formamide

Steps:

14.a a)
a) Preparation of ethyl 4,4-diethoxy-2-ethoxycarbonyl-butyrate Potassium tert-butoxide (141.8 g, 1.11 equiv.) was dissolved in dry DMF (1 L). Diethyl malonate (266 mL, 1.54 equiv.) was added over 5 minutes. Bromoacetaldehyde diethylacetal (172 mL, 1.14 mole) was added over 5 minutes. The mixture was heated to 120° C. (internal temperature), and stirred at 120° C. for 5 hours. The mixture was allowed to cool to room temperature, poured into water (5 L), and extracted with methyl tert-butyl ether (MTBE, 3*600 mL). The organic solution was dried over MgSO4, filtered, concentrated, and distilled (0.5 mm, 95-140° C.) to yield the desired diester (244 g, 78%) as a colorless oil. 1H NMR (CDCl3) δ 1.19 (t, 6H), 1.28 (t, 6H), 2.22 (dd, 2H), 3.49 (m, 2H), 3.51 (t, 1H), 3.65 (m, 2H) 4.20 (qd, 4H), 4.54 (t, 1H).

References:

Mediver AB US6184376, 2001, B2