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

HRID 1645388Notes

Reaction equation

HRID 1645388 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 1 (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 at RT for 20 hours. The reaction solution was poured into diethyl ether (300 ml), and the mixture was washed with water, sodium bicarbonate solution and sodium chloride solution. The solution was dried (Na2SO4), concentrated i. vac. and the colorless liquid which remained was processed further without purification.

Workup

  1. washthe mixture was washed with water, sodium bicarbonate solution and sodium chloride solution
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated i
  4. customand the colorless liquid which remained was processed further without purification

Sources & evidence

ORD record
ord-221a9022cef442af95dd61f5753f4099
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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