| Identification | Back Directory | [Name]
ETHYL 4-HYDROXYCYCLOHEXANECARBOXYLATE | [CAS]
17159-80-7 | [Synonyms]
Ai3-28355
Einecs 241-215-1
4-Hydroxycyclohexanecarboxylate
Ethyl 4-hydroxycyclohexanecarbonate
Ethyl 4-hydroxycyclohexylcarboxylate
ETHYL 4-HYDROXYCYCLOHEXANECARBOXYLATE
ethyl 4-hydroxycyclohexane-1-carboxylate
Ethyl4-hydroxycyclohexanecarboxylate,98%
4-Hydroxycyclohexane-1-carboxylic acid ethyl ester
Ethyl 4-hydroxycyclohexanecarboxylate≥ 99% (assay)
Cyclohexanecarboxylic acid, 4-hydroxy-, ethyl ester
Ethyl 4-hydroxycyclohexanecarboxylate, cis + trans, 97%
ETHYL 4-HYDROXYCYCLOHEXANECARBOXYLATE (cis-, trans-mixture)
Ethyl 4-hydroxycyclohexanecarboxylate,mixture of cis and trans
Ethyl 4-hydroxycyclohexanecarboxylate, Mixture of cis and trans 98%
Ethyl 4-hydroxycyclohexanecarboxylate, mixture of cis and trans ,98%
ETHYL 4-HYDROXYCYCLOHEXANECARBOXYLATE, 9 9%, MIXTURE OF CIS AND TRANS
Ethyl 4- Hydroxycyclohexanecarboxylate(Mixture of Cis & Trans isomers) | [EINECS(EC#)]
241-215-1 | [Molecular Formula]
C9H16O3 | [MDL Number]
MFCD00192156 | [MOL File]
17159-80-7.mol | [Molecular Weight]
172.22 |
| Chemical Properties | Back Directory | [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.)
| [Fp ]
>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 |
| Hazard Information | Back Directory | [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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