Sodium Hydroxide → 3-Cyclopentyl-2-phenylpropanoic acid

HRID 889599Notes

Reaction equation

HRID 889599 reaction equation
C[O:2][C:3](=[O:17])[CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>CO.O>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:3]([OH:17])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 462211553-Cyclopentyl-2-phenylpropionic acid methyl ester

Product 1

HCID 186266423-Cyclopentyl-2-phenylpropanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To title A compound, 3-cyclopentyl-2-phenylpropionic methyl ester (13.0 g, 56 mmol) in 100 mL of methanol is added a solution of 5.6 g (140 mmol) of NaOH in 8 mL of water. The reaction mixture is stirred at ambient temperature overnight. The methanol is evaporated and the residue is dissolved in 200 mL of water and extracted with ethyl ether. The aqueous phase is separated and adjusted to pH 2-3 with 1 N HCl and extracted with MTBE twice. The combined extracts are washed with saturated sodium chloride and dried over anhydrous magnesium sulfate. The material is evaporated to a yellow oil that crystallizes to provide 3-cyclopentyl-2-phenylpropionic acid as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 1.7 (m, 2H), 2.1 (m, 2H), 2.2 (m, 3H), 2.4(m, 3H), 2.4 (m, 1H), 4.2 (t, J=7.7 Hz, 1H), 7.9 (m, 5H); LC/MS 236 (M+NH4+).

Workup

  1. customThe methanol is evaporated
  2. dissolutionthe residue is dissolved in 200 mL of water
  3. extractionextracted with ethyl ether
  4. customThe aqueous phase is separated
  5. extractionextracted with MTBE twice
  6. washThe combined extracts are washed with saturated sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe material is evaporated to a yellow oil
  9. customthat crystallizes

Sources & evidence

ORD record
ord-3bc574c6b9864c999325dc5e769e919f
Source dataset
uspto-grants-2012_08
Patent number
US08252931B2

Reaction notes

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