Properties of substance:

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C₁₄H₂₄O₆

Structural formula as text:

(CH3O)2C(CH2)2C(COOCH(CH3)2)2

Synthesis 1:

Reference: Pigou, P. E., & Schiesser, C. H. Convenient route to 1,3-disubstituted cyclobutanes. An inexpensive synthesis of 3-oxocyclobutanecarboxylic acid / Journal of Organic Chemistry. - 1988. - Vol. 53, No. 16 pp. 3842 [doi: 10.1021/jo00251a033]

Diisopropyl malonate (376 g, 2.0 mol) was added in a dropwise manner, under nitrogen, to a stirred suspension of sodium hydride (52.8 g, 2.2 mol) in dry DMF (750 mL) at a rate such that the temperature was maintained below 70 °C. On cessation of hydrogen evolution, 1,3-dibromo-2,2-dimethoxypropane (267 g, 1.0 mol) was added in one portion and the mixture heated at 140 °C for 48 h. The conversion becomes very slow after the first 30 h, and reaction times in excess of 2 days are not warranted.

The cooled mixture was poured into an aqueous solution of ammonium chloride (100 g in 1.6 L), to prevent emulsion formation, and extracted with hexane. The combined extracts were then washed with water and sodium hydrogen carbonate solution and dried over magnesium sulfate, and the solvent was evaporated. Distillation of the residue through a short Vigreux column afforded a mixture of products in the more volatile (bp 68—85 °C/3 mm) fraction, consisting primarily of unreacted 1,3-dibromo-2,2-dimethoxypropane (0.40 mol) with some isopropyl 3,3-dimethoxycyclobutane-1-carboxylate (<0.02 mol). An air condenser was used to prevent clogging by 1,3-dibromo-2,2-dimethoxypropane (mp 62.5 °C) which could be recovered by filtration of the cooled distillate followed by recrystallization from methanol, returning 0.27 mol of the compound. Continued distillation then gave the required diester (161 g, 56%; 77% calculated on the spent dibromide) as a colorless oil with bp 92—94 °C (0.01 mm).

Calcd for C14H24O6: C, 58.3; H, 8.4. Found: C, 58.1; H, 8.3.

References:

What information do you need?