Sodium Hydroxide → 3-Cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

HRID 2185888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185888
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([O:15]C)=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].[OH-].[Na+]>C1COCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([OH:15])=[O:14])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 22452655Methyl 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

Produkt 1

HCID 224526443-Cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acidAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (0.96 g, 4.46 mmol) in THF (54 mL), water (21 mL) and 1N NaOH (9.4 mL, 9.4 mmol) was stirred overnight at room temperature. The THF was removed in vacuo and the mixture acidified to pH 1with 1N HCl. The resulting precipitate was extracted with EtOAc, dried (MgSO4), filtered and concentrated to give the title compound as a white solid (0.88 g, 98%). 1H NMR (DMSO) δ 13.33 (s, 1H), 7.96 (d, 1H), 7.29 (d, 1H), 3.99 (d, 2H), 2.81 (d, 2H), 1.72 (m, 4H); MS m/z 200.1 (M−H).

Aufarbeitung

  1. customThe THF was removed in vacuo
  2. extractionThe resulting precipitate was extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6d21d6da627c43709fb64a9ce32a8289
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06403601B1

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