Sodium Hydroxide → 4-[1-(4'-Tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid

HRID 1914316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1914316
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[OH-].[Na+]>C(O)C>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:17][CH:18]=2)=[CH:27][CH:26]=1)([CH3:30])([CH3:31])[CH3:29]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 671535394-[1-(4'-Tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid methyl ester

Produkt 1

HCID 671535284-[1-(4'-Tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of racemic 4-(1-hydroxy-3-methyl-butyl)-benzoic acid methyl ester (300 mg, 1.35 mmol) in toluene (14 mL) is added 1,1′-(azodicarbonyl)dipiperidine (ADDP, 512 mg, 2.03 mmol) at 0° C., followed by the addition of tributylphosphine (0.5 mL, 2.03 mmol) and 4′-tert butyl-biphenyl-4-ol (367 mg, 1.62 mmol). The reaction mixture is warmed up to room temperature and stirred overnight. The mixture is loaded on silica gel, eluted with hexanes with a gradient from 0% of ethyl acetate to 50% of ethyl acetate giving 4-[1-(4′-tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid methyl ester. The ester product is taken into ethanol (5 mL), treated with sodium hydroxide (5N aqueous, 1 mL) for 3 h at room temperature. The mixture is concentrated, diluted with ethyl acetate, acidified with 5 N HCl (1 mL), extract with ethyl acetate. The organic layers are dried and concentrated giving 4-[1-(4′-tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid (400 mg).

Aufarbeitung

  1. concentrationThe mixture is concentrated
  2. additiondiluted with ethyl acetate
  3. extractionextract with ethyl acetate
  4. customThe organic layers are dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-baa038c9ff784e499a7476a90457e051
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609892B2

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