DIETHYL 3-HYDROXYCYCLOBUTANE-1,1-DICARBOXYLATE

DIETHYL 3-HYDROXYCYCLOBUTANE-1,1-DICARBOXYLATE Property

Boiling point:

120-122 °C(Press: 3 Torr)

Density 

1.1108 g/cm3(Temp: 25 °C)

storage temp. 

2-8°C

pka

14.23±0.40(Predicted)

Appearance

Colorless to off-white Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

DIETHYL 3-HYDROXYCYCLOBUTANE-1,1-DICARBOXYLATE Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 3-hydroxy-1,1-cyclobutanedicarboxylic acid-1,1-diethyl ester from 3-(benzyloxy)cyclobutane-1,1-dicarboxylic acid is as follows: 3-(benzyloxy)cyclobutane-1,1-dicarboxylic acid-diethyl ester (2 g) was dissolved in ethanol (EtOH, 100 ml), and 10% palladium/carbon (Pd/C, 400 mg, 20% equiv) was added. The reaction suspension was subjected to hydrogenation at room temperature overnight. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure to afford the product 3-hydroxy-1,1-cyclobutanedicarboxylic acid-1,1-diethyl ester (1.3 g, 91.5% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) with the following chemical shifts: δ 2.44-2.49 (m, 2H), 2.85-2.90 (m, 2H), 4.35-4.37 (m, 1H), 4.21 (q, J=7.2 Hz, 4H), 1.26 (t, J=10.8 Hz, 6H).

References

[1] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8725 - 8733
[2] Synthesis (Germany), 2012, vol. 44, # 13, p. 2091 - 2101
[3] Patent: WO2009/8913, 2009, A2. Location in patent: Page/Page column 60
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2151 - 2155
[5] Patent: WO2010/70615, 2010, A1. Location in patent: Page/Page column 28; 29