Sodium Hydroxide → 3-Cyclopentyl-2-(4-nitrophenyl)propionic acid

HRID 889604Notes

Reaction equation

HRID 889604 reaction equation
C([O:3][C:4](=[O:21])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[OH-].[Na+]>CO>[CH:7]1([CH2:6][CH:5]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:4]([OH:21])=[O:3])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 114718493-Cyclopentyl-2-(4-nitro-phenyl)-propionic acid ethyl ester

Product 1

HCID 117371213-Cyclopentyl-2-(4-nitrophenyl)propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title A compound, 3-cyclopentyl-2-(4-nitro-phenyl)-propionic acid ethyl ester (3.6 g, 12.3 mmol) is dissolved in 25 mL of methanol and aqueous NaOH (0.70 g, 17.5 mmol in 4 mL of water) is added and the mixture is stirred at RT overnight. The methanol is removed under reduced pressure and the residue is diluted with 100 mL of water and extracted with ether. The aqueous layer is then acidified with 1N HCl and then extracted with ethyl acetate. The combined ethyl acetate layers are dried over anhydrous magnesium sulfate, filtered and reduced under vacuum to a crude orange oil. The crude oil is triturated with 100 mL of hexane/10-15 mL of ether to produce 3-cyclopentyl-2-(4-nitro-phenyl)-propionic acid as a solid: 1H NMR (400 MHz, CDCl3) δ 1.0-1.1 (m, 2H), 1.4-1.8 (m, 5H), 1.8-1.9 (m, 2H), 2.1-2.25 (m, 2H), 3.74 (t, 1H, J=7.8), 7.51 (d, 2H, J=8.8), 8.19 (d, 2H, J=8.8); LC/MS 218 (—CO2, M−1), 279 (M+NH4+).

Workup

  1. customThe methanol is removed under reduced pressure
  2. additionthe residue is diluted with 100 mL of water
  3. extractionextracted with ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined ethyl acetate layers are dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe crude oil is triturated with 100 mL of hexane/10-15 mL of ether

Sources & evidence

ORD record
ord-8e69cdea6b794b7b8dabeb9b24edae29
Source dataset
uspto-grants-2012_08
Patent number
US08252931B2

Reaction notes

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