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

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.

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

ORD-Eintrag

ord-7acf2b799cac4431a234b209a1175f8a

Quelldatensatz

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06355683B1