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

HRID 557510Notes

Reaction equation

HRID 557510 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Oxo-cyclohexanecarboxylic acid ethyl ester (52.8 g, 0.31 mol, Merck, Order No. 814249), ethylene glycol (67.4 g, 1.08 mol) and p-toluenesulfonic acid (0.7 g) in toluene (160 ml) were stirred for 20 h at RT; the reaction solution was poured into diethyl ether (300 ml) and washed with water, sodium hydrogen carbonate solution and sodium chloride solution. The solution was dried (Na2SO4) and concentrated in vacuo, and the colourless liquid that remained was processed further without being purified.

Workup

  1. washwashed with water, sodium hydrogen carbonate solution and sodium chloride solution
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customwithout being purified

Sources & evidence

ORD record
ord-89a55ffb942b468b8fc0f35a6c0c89c8
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

Loading…