ETHYL 4-HYDROXYCYCLOHEXANECARBOXYLATE Chemical Properties

Boiling point:

127-134 °C0.1 mm Hg(lit.)

Density 

1.068 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.466(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

liquid

pka

14.98±0.40(Predicted)

Specific Gravity

1.068

Appearance

Colorless to light yellow Liquid

Water Solubility 

Not miscible or difficult to mix in water.

InChI

InChI=1S/C9H16O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h7-8,10H,2-6H2,1H3

InChIKey

BZKQJSLASWRDNE-UHFFFAOYSA-N

SMILES

C1(C(OCC)=O)CCC(O)CC1

CAS DataBase Reference

17159-80-7

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2918199890

MSDS

• Language:English Provider:SigmaAldrich

ETHYL 4-HYDROXYCYCLOHEXANECARBOXYLATE Usage And Synthesis

Uses

Ethyl 4-hydroxycyclohexanecarboxylate, cis + trans is used in the synthesis of other chemicals and as pharmaceutical intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 4145, 1965 DOI: 10.1021/jo01023a039

Synthesis

General procedure for the synthesis of ethyl trans-4-hydroxycyclohexanecarboxylate from ethyl 4-oxocyclohexanecarboxylate: ethyl 4-oxocyclohexanecarboxylate (13.5 g, 79 mmol) was dissolved in methanol (150 mL) at 0 °C and sodium borohydride (5.3 g, 140 mmol) was added slowly. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (50 mL), followed by extraction with ethyl acetate (150 mL x 1, 50 mL x 2). The organic layers were combined, washed with water (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate, ratio 1.5:1 to 1:1) to afford ethyl 4-hydroxycyclohexanecarboxylate (12 g, 88% yield, cis-trans ratio = 3:7) as a clear oil.1H NMR (300 MHz, CDCl3, cis mixture) δ: 4.17-4.08 (m, 2H), 3.90 (bs. 0.3H), 3.68-3.57 (m, 0.7H), 2.42-1.28 (m, 9H), 1.27-1.22 (m, 3H) ppm.(Hydroxyl signal was not observed.)

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8967 - 9004
[2] Organic Process Research and Development, 2010, vol. 14, # 4, p. 883 - 889
[3] Patent: WO2005/80317, 2005, A2. Location in patent: Page/Page column 150
[4] Tetrahedron Letters, 2000, vol. 41, # 39, p. 7567 - 7570
[5] Patent: US5175290, 1992, A

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