3-(4-Cyano-2-ethyl-6-methyl-phenyl)-propionic acid ethyl ester → 3-(4-Cyano-2-ethyl-6-methylphenyl)propionic acid

HRID 2065909Notes

Reaction equation

HRID 2065909 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]#[N:15])=[CH:9][C:8]=1[CH2:16][CH3:17])C>C1COCC1.[OH-].[Na+].O>[C:14]([C:10]1[CH:11]=[C:12]([CH3:13])[C:7]([CH2:6][CH2:5][C:4]([OH:18])=[O:3])=[C:8]([CH2:16][CH3:17])[CH:9]=1)#[N:15]

Participants

5

Reactant 1

HCID 669320843-(4-Cyano-2-ethyl-6-methyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 574374143-(4-Cyano-2-ethyl-6-methylphenyl)propionic acidYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid ethyl ester (55.0 g, 224 mmol) in THF (220 mL) and 1N aq. NaOH solution (220 mL) is stirred at rt for 2 before it is diluted with water (200 mL) and extracted with DCM (2×200 mL). The aqueous phase is added to 32% aq. HCl solution (50 mL) at 15-30° C. A precipitate forms. The solid material is collected, washed with water and dried under high vacuum to give 3-(4-cyano-2-ethyl-6-methyl-phenyl)-propionic acid (40.87 g) as pale brown crystals; 1H NMR (D6-DMSO): δ 1.17 (t, J=7.5 Hz, 3H), 2.30-2.39 (m, 5H), 2.67 (q, J=7.3 Hz, 2H), 2.87-2.94 (m, 2H), 7.47 (s, 2H), 12.30 (s, 1H).

Workup

  1. extractionextracted with DCM (2×200 mL)
  2. additionThe aqueous phase is added to 32% aq. HCl solution (50 mL) at 15-30° C
  3. customThe solid material is collected
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-069e2f09feb74cf5ae09cdc994d70150
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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