Hydrochloric Acid → HCID 67486632, compound

HRID 2371271Notes

Reaction equation

HRID 2371271 reaction equation
C([O:8][C:9](=[O:31])[CH:10]([C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)C1C=CC=CC=1.[OH-].[Na+].Cl>O1CCCC1.CO.O>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([CH:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:9]([OH:31])=[O:8])=[CH:26][CH:25]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67486784HCID 67486784, compound

Product 1

HCID 67486632HCID 67486632, compoundYield 119.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To 2-(4-tert-Butyl-phenyl)-3-(4-nitro-phenyl)-propionic acid benzyl ester (8.6 g, 20.6 mmol) in 30 ml tetrahydrofuran, 20 ml methanol and 10 ml water was added sodium hydroxide (0.6 g, 24.7 mmol). The reaction mixture was stirred at 23° C. for 16 h, acidified with 4N hydrochloride acid, and concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was washed with water, dried over magnesium sulfate, and concentrated to afford 2-(4-tert-Butyl-phenyl)-3-(4-nitro-phenyl)-propionic acid as a brownish oil (8.04 g, 100%).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-45b60e9b461144dd80813bbd3c227991
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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