Ethylene Glycol → HCID 12869104, compound

HRID 73622

Reaction equation

HRID 73622 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])=[O:4].[CH2:12](O)[CH2:13][OH:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:14]1[C:6]2([CH2:7][CH2:8][CH2:9][CH2:10][CH:5]2[C:3]([O:2][CH3:1])=[O:4])[O:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 170489Cyclohexanecarboxylic acid, 2-oxo-, methyl esterHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 12869104HCID 12869104, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of methyl-2-oxocyclohexanecarboxylate (4-1) (7.0 g, 44.8 mmol), ethylene glycol (3.00 mL, 53.8 mmol) and p-toluenesulfonic acid monohydrate (0.853 g, 4.48 mmol) in Benzene (45 mL) was heated to reflux overnight. The reaction was then cooled to rt and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 3.86-3.99 (m, 4H), 3.69 (s, 3H), 2.69 (dd, 1H, J=4.9 Hz, 9.0 Hz), 1.82-1.97 (m, 3H), 1.58-1.73 (m, 3H), 1.45-1.53 (m, 1H), 1.26-1.37 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e941809fc46f44f69bbcda672120d6df
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Linked notes

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