Sodium Hydroxide → HCID 58066385, compound

HRID 2410539Notes

Reaction equation

HRID 2410539 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[C:10]([C:12]([O:14]C)=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH3:23])[CH3:4]>CCO>[CH2:3]([O:5][C:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[CH:9]=[CH:8][C:7]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH3:23])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66678423HCID 66678423, compound

Product 1

HCID 58066385HCID 58066385, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A 5N aqueous solution of NaOH (3 mL, 15 mmol) was added into a solution of methyl 2-ethoxy-2′-ethylbiphenyl-4-carboxylate (2.72 g, 9.6 mmol) in EtOH (30 mL). The resulting mixture was heated at 60° C. for 1 hour. The reaction mixture was concentrated under vacuum. The residue was taken up with water (50 mL) and a 5N aqueous solution of HCl (5 mL), and then extracted twice with MTBE (100 mL+50 mL). The organic layers were washed with brine (50 mL), combined, dried (MgSO4) and concentrated under vacuum. After purification by crystallization from MTBE and heptane, the title compound was obtained as a white powder (2.04 g, 79%). HPLC (Method A) Rt 4.5 min (Purity: 100%). LC/MS (Method B): 269.1 (M−H)−. 1H NMR (DMSO-d6, 300 MHz) δ 13.00 (s, 1H), 7.58 (m, 2H), 7.30 (m, 2H), 7.22 (m, 2H), 7.06 (d, J=7.4 Hz, 1H), 4.05 (q, J=7.0 Hz, 2H), 2.45-2.32 (m, 2H), 1.17 (t, J=7.0 Hz, 3H), 0.97 (t, J=7.6 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. extractiona 5N aqueous solution of HCl (5 mL), and then extracted twice with MTBE (100 mL+50 mL)
  3. washThe organic layers were washed with brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuum
  6. customAfter purification
  7. customby crystallization from MTBE and heptane

Sources & evidence

ORD record
ord-e6bcdc8900b4411badad25f43d1e20ec
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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