ChemicalBook CAS DataBase List ethyl 2-(4-hydroxycyclohexyl)acetate

ethyl 2-(4-hydroxycyclohexyl)acetate synthesis

7synthesis methods

Product Name:ethyl 2-(4-hydroxycyclohexyl)acetate
CAS Number:62141-22-4
Molecular formula:C10H18O3
Molecular Weight:186.25

17138-28-2
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62141-22-4
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Yield:62141-22-4 100%

Reaction Conditions:

with hydrogen;5 weight % Rh on alumina in ethanol; under 3102.97 Torr; for 56 h;

Steps:

1.3.B

Method B; Ethyl (4-hydroxyphenyl)acetate (5Og, 277 mmol) was dissolved in 150 niL of ethanol in a Parr bottle with Rh/Al₂O₃ (1.00 g, 5 wt%, Aldrich Lot:07727AB). The suspension was hydrogenated on a Parr shaker at 60 psi. After 48 h, starting material was still present, so additional Rh/ Al₂O₃ (4.00 g) was added. The suspension was hydrogenated for another 8 h, at which time a sample analyzed by ¹H NMR indicated the reaction was complete. The reaction mixture was filtered through Celite and rinsed with ethanol (450 mL). The reaction mixture was concentrated to afford a clear colorless oil (55.0 g, quantitative).The resulting ethyl (4-hydroxycyclohexyl)acetate (45.0 g, 240 mmol) was dissolved in AcOH (160 mL) and slowly treated with NaOCl (171 mL, 10-13% available chlorine, -1.7 M, -290 mmol) to maintain the temperature below 30 °C. Brine (500 mL) was added to the solution and the aqueous layer was extracted withEtOAc (3X500 mL). The organic layers were combined, washed with brine (500 mL), concentrated to an oil and chased with heptane. ¹H NMR indicated ~1 equivalent of AcOH. The oil was redissolved in EtOAc (500 mL), washed with sat. NaHCO₃ (2X250 mL) and brine (200 mL). The organic layer was collected, dried (Na₂SO₄), filtered, and concentrated to yield 40.7 g (92%) of a clear colorless oil. ¹HNMR (DMSO-d₆) 64.05 (q, 2H), 2.39 (dt, 2H), 2.30 (d, 2H), 2.19-2.14 (m, 3H), 1.96-1.90 (m, 2H), 1.39 (dq, 2H), 1.18 (t, 3H). GCMS (EI) RT = 9.3 min, [M]+ = 184.