Sodium Hydroxide → 3-Benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylic Acid

HRID 1953964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953964
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[S:11][C:10]=1[C:18]([O:20]C)=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[S:11][C:10]=1[C:18]([OH:20])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 15477099Methyl 3-Benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylate

Produkt 1

HCID 154771003-Benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylic AcidAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-benzyloxy-5-(methylsulfonyl)-2-thiophenecarboxylate (16.7 g, 51.2 mmol), 50 ml 2N NaOH and 50 ml of tetrahydrofuran is heated at reflux temperatures for 1 hour, cooled to room temperature and concentrated in vacuo to an aqueous residue. The residue is diluted with water, acidified to pH 1-2 with 6N HCl and filtered. The filtercake is washed with water and dried to give the title product as a white solid, 14.55 g (91% yield). A small sample was recrystallized from aqueous ethanol to give white needles, mp 188-189° C., identified by 1HNMR, 13CNMR, IR and mass spectral analyses.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperatures for 1 hour
  3. concentrationconcentrated in vacuo to an aqueous residue
  4. additionThe residue is diluted with water
  5. filtrationfiltered
  6. washThe filtercake is washed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0427b91fb64346f7a779dd283a6de8a2
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06121202

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