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

HRID 1665916Notes

Reaction equation

HRID 1665916 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 methanol (140 mL) and 2 N aq. NaOH (45 mL) is stirred at rt for 1 h. The methanol is evaporated and the aq. solution is extracted twice with DCM. The aq. layer is acidified with 37% aq. HCl. The precipitate that forms is collected, washed with water and dried. The product is further purified by recrystallisation from EA (100 mL) to give 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid (4.2 g) as yellow crystals; LC-MS: tR=0.87 min.

Workup

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

Sources & evidence

ORD record
ord-e523ec79ade6425ea3c5d5aaf5b89d44
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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