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

HRID 1821635Notes

Reaction equation

HRID 1821635 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-oxocyclohexane carboxylic acid ethyl ester 9 (52.8 g, 0.31 mole, 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 hours at RT, and 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), concentrated by evaporation in vacuo, and the remaining colorless liquid was processed further without purification.

Workup

  1. washwashed with water, sodium hydrogen carbonate solution and sodium chloride solution
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated by evaporation in vacuo
  4. customthe remaining colorless liquid was processed further without purification

Sources & evidence

ORD record
ord-d1af912740f2481a82d087d34a262ac2
Source dataset
uspto-grants-2009_10
Patent number
US07608619B2

Reaction notes

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