3-(2-Ethyl-4-formyl-6-methyl-phenyl)propenoic acid methyl ester → 3-(2-Ethyl-4-formyl-6-methyl-phenyl)-acrylic acid

HRID 1958772Notes

Reaction equation

HRID 1958772 reaction equation
C[O:2][C:3](=[O:17])[CH:4]=[CH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH:13]=[O:14])=[CH:8][C:7]=1[CH2:15][CH3:16]>CO.[OH-].[Na+]>[CH2:15]([C:7]1[CH:8]=[C:9]([CH:13]=[O:14])[CH:10]=[C:11]([CH3:12])[C:6]=1[CH:5]=[CH:4][C:3]([OH:17])=[O:2])[CH3:16]

Participants

4

Reactant 1

HCID 765393103-(2-Ethyl-4-formyl-6-methyl-phenyl)propenoic acid methyl ester

Product 1

HCID 765393093-(2-Ethyl-4-formyl-6-methyl-phenyl)-acrylic acidYield 75.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid methyl ester (5.93 g, 25.53 mmol) in MeOH (140 mL) and 2 N aq. NaOH (45 mL) was stirred at rt for 1 h. The MeOH was evaporated and the aq. solution was extracted twice with DCM. The aq. layer was acidified with 37% aq. HCl. The precipitate that formed was collected, washed with water and dried. The product was further purified by recrystallisation from EA (100 mL) to give 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid as yellow crystals (4.2 g). LC-MS: tR=0.87 min.

Workup

  1. customThe MeOH was evaporated
  2. extractionthe aq. solution was extracted twice with DCM
  3. customThe precipitate that formed
  4. customwas collected
  5. washwashed with water
  6. customdried
  7. customThe product was further purified by recrystallisation from EA (100 mL)

Sources & evidence

ORD record
ord-2ca050fa7d4d4da981888b38f524133e
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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