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

HRID 733075Notes

Reaction equation

HRID 733075 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-Oxocyclohexanecarboxylic 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 poured into diethyl ether (300 ml) and washed with water, sodium hydrogencarbonate solution and sodium chloride solution. The solution was dried (Na2SO4), evaporated under a vacuum and the remaining colorless liquid further processed without purification.

Workup

  1. washwashed with water, sodium hydrogencarbonate solution and sodium chloride solution
  2. dry with materialThe solution was dried (Na2SO4)
  3. customevaporated under a vacuum
  4. customthe remaining colorless liquid further processed without purification

Sources & evidence

ORD record
ord-f7ba9176b7b94719937654c072506e9e
Source dataset
uspto-grants-2009_09
Patent number
US07589113B2

Reaction notes

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