ChemicalBook CAS DataBase List 4-HYDROXYCYCLOHEXANONE

4-HYDROXYCYCLOHEXANONE synthesis

13synthesis methods

Product Name:4-HYDROXYCYCLOHEXANONE
CAS Number:13482-22-9
Molecular formula:C6H10O2
Molecular Weight:114.14

4-Hydroxycyclohexanone can be used as an intermediate in organic synthesis. It can be obtained from 1,4-dioxaspiro[4,5]cyclohexan-8-one as raw material is reduced by sodium borohydride and deprotected.

556-48-9
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13482-22-9
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Yield:13482-22-9 91%

Reaction Conditions:

with sodium bromate;ammonium cerium (IV) nitrate in water;acetonitrile for 2.5 h;Reflux;

Steps:

1 Step 1: 4-hydroxycyclohexanone
Cerium (IV) ammonium nitrate (45.4 g, 82.85 mmol) and sodium bromate (125 g, 0.828 mol) were added to a solution of 1 ,4-cyclohexanediol (commercially available from Sigma-Aldrich, Milwaukee, WI, 278 g, 2.393 mol) in ACN (2.7 L) and water (1.15 L). The resulting mixture was heated at reflux for 2.5 hours and then cooled to room temperature. The resulting solution was extracted with chloroform (1 L x 3), and the combined organic extracts were dried, filtered and concentrated to afford 4-hydroxycyclohexanone (245 g, 91%). m/z (ESI) 1 15 (M+H)⁺.

References:

AMGEN INC.;BREGMAN, Howard;BUCHANAN, John, L.;CHAKKA, Nagasree;DIMAURO, Erin;GUNAYDIN, Hakan;GUZMAN PEREZ, Angel;HUA, Zihao;HUANG, Hongbing;HUANG, Xin;MARTIN, Matthew, W.;PATEL, Vinod WO2013/134079, 2013, A1 Location in patent:Paragraph 0219-0220

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123-31-9 Synthesis