Sodium Hydroxide → 1,3-Bis(m-carboxyphenyl)-1-propanol

HRID 277296

Reaktionsgleichung

Reaktionsgleichung von HRID 277296
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([OH:22])=[O:21])[CH:15]=2)=[O:13])[CH:7]=[CH:8][CH:9]=1)([OH:3])=[O:2].[OH-].[Na+].[BH4-].[Na+]>C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:20]([C:16]1[CH:15]=[C:14]([CH:12]([OH:13])[CH2:11][CH2:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[CH:19]=[CH:18][CH:17]=1)([OH:22])=[O:21]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 538375063,3'-Dicarboxychalcone

Produkt 1

HCID 226017891,3-Bis(m-carboxyphenyl)-1-propanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)KatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

3,3′-Dicarboxychalcone (Example 4, step 2) (430 mg, 1.45 mmol) in ethanol (10 mL) containing aqueous NaOH (1 M, 2.90 mmol) was hydrogenated at 45 psi for 48 hours in the presence of Wilkinson's catalyst (67 mg, 0.07 mmol). The reaction mixture was filtered and concentrated in vacuo. The residue was dissolved in methanol (10 mL) and treated with NaBH4 (220 mg, 5.8 mmol) at rt. The reaction mixture was stirred for 16 hours at rt, quenched with the cautious addition of saturated aqueous NH4Cl and partitioned between EtOAc (50 mL) and aqueous HCl (1 M, 50 mL). The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to give 1,3-bis (m-carboxyphenyl)-1-propanol as a viscous oil. MS (APCI) m/z 299 (M+−1, 100%). 1H NMR (200 MHz, CDCl3); δ1.95-2.10, m, 2H; 2.68-2.83, m, 2H; 4.62-4.78, m, 1H; 7.03-7.60, m, 4H; 7.75-8.03, m, 4H.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in methanol (10 mL)
  4. customquenched with the cautious addition of saturated aqueous NH4Cl
  5. custompartitioned between EtOAc (50 mL) and aqueous HCl (1 M, 50 mL)
  6. extractionThe organic extract
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7acf2b799cac4431a234b209a1175f8a
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355683B1

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