Ethylene Glycol → HCID 21834550, compound

HRID 1741026Notes

Reaction equation

HRID 1741026 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 (D3, 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-c9d6b5de4f0a4a4b9e1d3f98eb40048b
Source dataset
uspto-grants-1999_10
Patent number
US05972979

Reaction notes

Loading…