3-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester → 3-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid

HRID 1665906Notes

Reaction equation

HRID 1665906 reaction equation
C[O:2][C:3](=[O:16])[CH:4]=[CH:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH:13]=[O:14])=[CH:8][C:7]=1[CH3:15]>CO.[OH-].[Na+]>[CH:13]([C:9]1[CH:10]=[C:11]([CH3:12])[C:6]([CH:5]=[CH:4][C:3]([OH:16])=[O:2])=[C:7]([CH3:15])[CH:8]=1)=[O:14]

Participants

4

Reactant 1

HCID 765393073-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester

Product 1

HCID 765393083-(4-Formyl-2,6-dimethyl-phenyl)-acrylic acidYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid methyl ester (2.9 g, 13.3 mmol) in methanol (70 mL), 2 N aq. NaOH (35 mL) is added. The suspension is stirred for 30 min at rt. Methanol is evaporated and the aq. solution is extracted twice with DCM. The aq. layer is acidified with 2 N aq. HCl and extracted twice with EA. The combined EA extracts are dried over MgSO4, filtered and evaporated. The crude product is recrystallized from EA to give 3-(4-formyl-2,6-dimethyl-phenyl)-acrylic acid (2.2 g) as pale yellow crystals; LC-MS: tR=0.83 min; 1H NMR (D6-DMSO): δ 12.65 (s br, 1H), 9.92 (s, 1H), 7.66 (d, J=16.4 Hz, 1H), 7.61 (s, 2H), 6.12 (d, J=16.4 Hz, 1H), 2.35 (s, 6H).

Workup

  1. customMethanol is evaporated
  2. extractionthe aq. solution is extracted twice with DCM
  3. extractionextracted twice with EA
  4. dry with materialThe combined EA extracts are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is recrystallized from EA

Sources & evidence

ORD record
ord-316e295907ca4a5ab777034fb2232d10
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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