Ethylene Glycol → HCID 86608910, compound

HRID 596112Notes

Reaction equation

HRID 596112 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=O)[CH2:4][CH2:3]1.[CH2:13]([OH:16])[CH2:14][OH:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOCC>[CH2:13]1[O:16][C:8]([CH:5]2[CH2:4][CH2:3][C:2](=[O:1])[CH2:7][CH2:6]2)([O:10][CH2:11][CH3:12])[O:15][CH2:14]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 86608910HCID 86608910, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethyl 4-oxocyclohexanecarboxylate (15.01 g, 88.16 mmol) was combined with ethylene glycol (21 mL, 4.27 equiv.) and p-toluenesulfonic acid monohydrate (0.2 g, 0.012 equiv.) in anhydrous toluene (50 mL), and the mixture was stirred 14 h at room temperature. The reaction was diluted with ether (200 mL) and was washed with H2O (2×200 mL), saturated sodium bicarbonate (100 mL) and brine (80 mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure to yield 18.15 g ethyl 4-oxocyclohexanecarboxylate ethylene ketal (96% yield). LCMS (m/z): 214.8 (MH+), 0.74 min.

Workup

  1. washwas washed with H2O (2×200 mL), saturated sodium bicarbonate (100 mL) and brine (80 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cdcf3fd2e4624b87ae34bf7b3345d042
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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