To synthesize 5, 5-dimethylcyclohexan-1, 3-dione by means of the Robinson annulation from diethyl

propanedioate and 4-Methylene pent-3-en-2-one as well as to test the purification of the product by
measuring the melting temperature and performing a Thin Layer Chromatography. Introduction: The
Robinson annulation is used for the synthesis of six-membered ring compounds, especially for
steroids 1. It consists of a Michael addition to yield an intermediate compound which then
undergoes an intramolecular aldol condensation under the reaction conditions. In this
experiment5,5-dimethylcyclohexane-1,3-dione(dimedone) is synthesized. This synthesis is a
modification of the normal Robinson annulation where the initial Michael addition of diethyl
malonate with 4-methylpent-3-en-2-one is followed by an intramolecular Claisen condensation
rather than aldol condensation. The annulation product is hydrolysed and decarboxylated to yield
the cyclic 1,3-diketone 2.Figure 1: Synthesis of 5,5-dimethylcyclohexane-1,3-dioneThin layer
chromatography (TLC) is based on a multistage distribution process. This process involves: a suitable
adsorbent (the stationary phase), solvents or solvent mixtures (the mobile phase or eluent), and the
sample molecules. The adsorbent is coated as a thin layer onto a suitable support (e.g. glass plate,
polyester or aluminium sheet). On this layer the substance mixture is separated by elution with a
suitable solvent

Results and Calculations:

Diethyl propanedioate/Diethyl malonate (C7H12O4)

Molar mass: 160.17g/mol

Volume: 8.5 mL

Density: 1.05 g/mL

Mass = Density × Volume= 1.05g/mL × 8.5mL= 8.93g

Number of moles: mass/molar mass = 8.93g / 160.17g. mol−1 =0.056mol =56 mmol

4-Methylene pent-3-en-2-one/Mesityl oxide (C6H10O)

Molar mass: 98.14g/mol

Volume: 6 mL

Density: 0.858 g/mL

Mass = Density × Volume= 0.858g/mL ×6mL= 5.15g

Number of moles: mass/molar mass = 5.15g / 98.14g. mol−1=0.0524mol= 52.4 mmol

There is a 1:1 stoichiometric ratio between Diethyl propanedioate and 4-Methylene pent-3-en-2-one
when reacting, therefore 4-Methylene pent-3-en-2-one is the limiting reagent. The maximum
amount of 5, 5-dimethylcyclohexan-1,3-dione that can be formed is therefore 52.4 mmol
5, 5-dimethylcyclohexan-1,3-dione /Dimedone(C8H12O2)

Mass of product :5.64g

Molar mass=140.18g/mol

Number of moles: mass/ molar mass = 5.64g / 140.18g. mol−1=0.0402mol=40.23mmol

Percentage yield = (experimental yield / theoretical yield) ×100%

= (40.23mmol / 52.4mmol) × 100%= 76.77 %

TLC

Rf=Distance travelled by the compound/Distance covered by the solvent front

Starting material Rf=3.7cm/4.1cm=0.902

Product Rf=1.5cm/4.1cm=0.366

Melting point (from literature): 146-148 °C(lit.)

The product formed light orange crystals.