Sodium Hydroxide → 2-(p-Toluenesulfonyloxy)acetic Acid

HRID 2422920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422920
[S:1]([O:11][CH2:12][C:13]([O:15]CC)=[O:14])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH-].[Na+]>C(O)C>[S:1]([O:11][CH2:12][C:13]([OH:15])=[O:14])([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 11821264Ethyl 2-(p-Toluenesulfonyloxy)acetate

Produkt 1

HCID 2262662-(p-Toluenesulfonyloxy)acetic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-(tosyloxy)acetate (2, 860 mg, 3.33 mmol) in ethanol (4 ml) was treated at room temperature with 5% NaOH aqueous solution (2 ml). The resulting mixture was stirred at room temperature for 3 h. The ethanol was removed in vacuo and aqueous 5% HCl solution (2.7 ml) was added. The aqueous mixture was extracted with chloroform and the organic extracts dried (Na2SO4), filtered and the solvent removed under reduced pressure. The remaining white solid was recrystallized from hexane/ethyl acetate as a white powder (476 mg, 62%). [This reaction was repeated on 2× scale (1.449 g, 94%)]. δH (400 MHz, MeOD) 2.45 (3H, s, Me), 4.58 (2H, s, CH2), 7.44 (2H, d, J=8.2 Hz, ArH), 7.82 (2H, d, J=8.2 Hz, ArH); δc (100.6 MHz, MeOD) 20.4, 64.7, 128.0, 129.9, 133.0, 145.6, 168.2; MS (ES+) 247.8 (100%, [M+H2O]+); MS (ES−) 170.1 (100%, TsO−).

Aufarbeitung

  1. customThe ethanol was removed in vacuo and aqueous 5% HCl solution (2.7 ml)
  2. additionwas added
  3. extractionThe aqueous mixture was extracted with chloroform
  4. dry with materialthe organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe remaining white solid was recrystallized from hexane/ethyl acetate as a white powder (476 mg, 62%)

Quellen und Nachweise

ORD-Eintrag
ord-a0dc166af4a84344839a951390973bd9
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960434B2

Notizen zur Reaktion

Wird geladen…