Ethylene Glycol → HCID 21834550, compound

HRID 617743Notes

Reaction equation

HRID 617743 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:15]([OH:17])=[O:16])[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:30](O)[CH2:31][OH:32]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:15]([OH:17])=[O:16])[CH2:9][CH2:10][C:11]2([O:32][CH2:31][CH2:30][O:14]2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 219552001-(2-Fluorophenyl)-4-oxocyclohexanecarboxylic acid

Product 1

HCID 21834550HCID 21834550, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(2-Fluorophenyl)-4-oxocyclohexane-1-carboxylic acid (D20, 16.36 g, 69 mmol) was stirred with toluene-4-sulphonic acid hydrate (0.50 g, 3 mmol) and 1,2-ethanediol (35 ml) at reflux in toluene (500 ml), removing the immiscible 1,2-ethanediol/water distillate via a Dean-Stark trap until the distillate was homogenous. The solution was then evaporated, dissolved in ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated to give the title compound (19.94 g, quantitative) as an amber syrup, contaminated with some unidentified materials (NMR).

Workup

  1. customremoving the immiscible 1,2-ethanediol/water distillate via a Dean-Stark trap until the distillate
  2. customThe solution was then evaporated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-4cc8fc5f12bd4585ba65901de5bec013
Source dataset
uspto-grants-1999_09
Patent number
US05952325

Reaction notes

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