Hydrochloric Acid → 4'-Cyano-6-methyl-biphenyl-3-carboxylic acid

HRID 1924797

Reaktionsgleichung

Reaktionsgleichung von HRID 1924797
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=2)[C:8]([CH3:11])=[CH:9][CH:10]=1)=[O:4].[OH-].[Na+].Cl>O1CCOCC1.O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:7]2[C:8]([CH3:11])=[CH:9][CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=2)=[CH:13][CH:14]=1)#[N:19]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 594367074'-Cyano-6-methyl-biphenyl-3-carboxylic acid methyl ester

Produkt 1

HCID 594367094'-Cyano-6-methyl-biphenyl-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a solution of 4′-cyano-6-methyl-biphenyl-3-carboxylic acid methyl ester 2 (2.56 g, 10.3 mmol) in 1,4-dioxane-H2O (1:1 mixture, 20 ml) is added NaOH (1.22 g, 30.2 mmol)). The reaction is stirred at ambient temperature for 24 hours. To this mixture is added aqueous HCl (1 N, 36 ml) and it is then extracted with ethyl acetate (40 ml×3). The organic layers are combined, dried over anhydrous Na2SO4. The solver is removed. The solid obtained is washed with small amount of acetonitrile and air dried to give 4′-cyano-6-methyl-biphenyl-3-carboxylic acid 3: 1H NMR (DMSO-d6) δ 7.94 (d, 2 H, J=8.0 Hz), 7.84 (dd, 1 H, J1=8.4 Hz, J2=1.2 Hz), 7.75 (d, 1 H, J=1.2 Hz), 7.61 (d, 2 H, J=8.0 Hz), 7.48 (d, 1 H, J=8.4 Hz), 2.29 (s, 3H); LC-MS m/z 238.1 (M+1).

Aufarbeitung

  1. extractionis then extracted with ethyl acetate (40 ml×3)
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solver is removed
  4. customThe solid obtained
  5. washis washed with small amount of acetonitrile and air
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-88cca433582b49a1a839d7c68fea0261
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178563B2

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