Ethylene Glycol → 2-[3-(Naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-ethanol

HRID 2240014Notes

Reaction equation

HRID 2240014 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:22]([O-:24])=[O:23])=[C:6]([CH2:8][S:9]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1.[CH2:25]([OH:28])[CH2:26][OH:27].C1COCC1>CC(C)([O-])C.[K+]>[C:12]1([S:9]([CH2:8][C:6]2[CH:7]=[C:2]([CH:3]=[CH:4][C:5]=2[N+:22]([O-:24])=[O:23])[O:27][CH2:26][CH2:25][OH:28])(=[O:11])=[O:10])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 8028TetrahydrofuranHCID 593041751-(5-Fluoro-2-nitrobenzylsulfonyl)naphthalene

Product 1

HCID 588120652-[3-(Naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-ethanolYield 87.3%

Reagents, catalysts & solvents 1

HCID 23665647Potassium tert-butoxideSolvent

Procedure

A mixture of 1-(5-fluoro-2-nitro-phenylmethanesulfonyl)-naphthalene (14.6 g, 42.3 mmol) and ethylene glycol (35 mL, 630 mmol) in 1.0 N potassium tert-butoxide in THF (90 mL, 90 mmol) was refluxed under nitrogen for one hour. After cooling to ambient temperature, the reaction mixture was concentrated. Excess water was added to the residue, and the mixture was poured into ice/2N hydrochloric acid. It was extracted with ethyl acetate and washed with water and brine. It was then dried with anhydrous magnesium sulfate, filtered, concentrated and dried in vacuo at 80° C. for 25 minutes to yield 2-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-ethanol as a brown gum (14.3 g, 87.2%). Mass Spectrum (−EI, [M−H]−) m/z 386. 1HNMR (500 MHz, DMSO-d6): δ8.56-8.57 (m, 1H), 8.35 (d, 1H, J=8.24 Hz), 8.14-8.15 (m, 1H), 8.00-8.02 (m, 2H), 7.65-7.75 (m, 3H), 7.11-7.13 (m, 1H), 6.89 (d, 1H, J=2.90 Hz), 5.27 (s, 2H), 4.92 (t, 1H, J=5.49 Hz), 3.93-3.95 (m, 2H), 3.67 ppm (dd, 2H, J=9.91 Hz and 5.34 Hz). Elemental Analysis for C19H17NO6S.0.25 mol H2O: Calcd: C, 58.23; H, 4.50; N, 3.57; Found: C, 57.83; H, 4.25; N, 3.50.

Workup

  1. temperaturewas refluxed under nitrogen for one hour
  2. concentrationthe reaction mixture was concentrated
  3. additionExcess water was added to the residue
  4. additionthe mixture was poured into ice/2N hydrochloric acid
  5. extractionIt was extracted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialIt was then dried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried in vacuo at 80° C. for 25 minutes

Sources & evidence

ORD record
ord-8f781d02efb34d74b08f42c649a8d2b0
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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