Ethylene Glycol → HCID 58812110, compound

HRID 2239986Notes

Reaction equation

HRID 2239986 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[C:15](F)[CH:14]=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]([OH:24])[CH2:22][OH:23].CC(C)([O-])C.[K+]>C1COCC1>[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[C:15]([CH:14]=[CH:13][C:12]=2[N+:18]([O-:20])=[O:19])[O:23][CH2:22][CH2:21][OH:24])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 131807962-[(Benzenesulfonyl)methyl]-4-fluoro-1-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 58812110HCID 58812110, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 2-benzenesulfonylmethyl-4-fluoro-1-nitrobenzene (10.2 g, 34.7 mmol), ethylene glycol (80 mL, 1.4 mol), and 1 M potassium tert-butoxide in THF (78 mL, 78 mmol) in THF (50 mL) was refluxed under nitrogen for 30 minutes. After cooling to about ambient temperature, the reaction mixture was solvent evaporated. Water was added to the residue, and it was poured into 2.0 N hydrochloric acid and ice. The mixture was then extracted with ethyl acetate and washed with water and brine. The organic phase was dried with anhydrous magnesium sulfate, filtered, concentrated and dried in vacuo at 74° C. for 20 minutes. 2-(3-Benzenesulfonylmethyl-4-nitro-phenoxy)-ethanol as a dark brown gum (11.7 g, 100% yield) was obtained; Mass spectrum (−EI, [M−H]−) m/z 336. 1HNMR (500 MHz, DMSO-d6): δ8.01 (d, 1H, J=9.15 Hz), 7.67-7.73 (m, 1H), 7.54-7.63 (m, 4H), 7.10 (dd, 1H, J=9.51 Hz and 2.93 Hz), 6.85 (d, 1H, J=2.81 Hz), 5.12 (s, 2H), 4.88-4.90 (m, 1H), 3.93-3.96 (m, 2H), 3.65 ppm (d, 2H, J=4.51 Hz). Elemental Analysis for C15H15NO6S: Calcd: C, 53.41; H, 4.48; N, 4.15; Found: C, 53.47; H, 4.69; N, 4.04;

Workup

  1. temperaturewas refluxed under nitrogen for 30 minutes
  2. temperatureAfter cooling to about ambient temperature
  3. customevaporated
  4. additionWater was added to the residue, and it
  5. additionwas poured into 2.0 N hydrochloric acid and ice
  6. extractionThe mixture was then extracted with ethyl acetate
  7. washwashed with water and brine
  8. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried in vacuo at 74° C. for 20 minutes

Sources & evidence

ORD record
ord-0bcaa89b7c37473da90719afdceb2529
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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