Ethylene Glycol → Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

HRID 1879082Notes

Reaction equation

HRID 1879082 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC=CC=1>CCOCC>[O:15]1[C:2]2([CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)[O:1][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of ethyl 4-oxocyclohexanecarboxylate (25 g), 10-campharsulfonic acid, ethylene glycol (40 mL), and toluene (400 mL) was heated under reflux with a Dean-Stark apparatus for 2.5 h (bath temp. 135° C.). The mixture was cooled down, and then was diluted with ether (200 mL). After the ethylene glycol layer was separated, the organic layer was washed with saturated aqueous sodium bicarbonate solution (2×) and brine (1×), dried over MgSO4, and filtered. The filtrate was evaporated in vacuo to give 2 as an oil (31.29 g, 99%): 1H NMR (CDCl3) δ 4.13 (2H, q, J=7.1 Hz), 3.95 (4H, s), 2.33 (1H, m), 1.93 (2H, m), 1.79 (4H, m), 1.56 (2H, m) 1.25 (3H, t, J=7.1 Hz); 13C NMR (CDCl3) δ 175.4, 108.3, 64.5, 60.5, 41.8, 33.9, 26.5, 14.4.

Workup

  1. temperaturewas heated
  2. temperatureThe mixture was cooled down
  3. customAfter the ethylene glycol layer was separated
  4. washthe organic layer was washed with saturated aqueous sodium bicarbonate solution (2×) and brine (1×)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-497eaa246307417c8a96a517cc97ae61
Source dataset
uspto-grants-2012_11
Patent number
US08314137B2

Reaction notes

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