Water → [3-(2-Formyl-4-trifluoromethyl-phenoxy)-4-methoxy-phenyl]-acetic acid methyl ester

HRID 885255Notes

Reaction equation

HRID 885255 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([OH:13])[CH:6]=1.F[C:16]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:17]=1[CH:18]=[O:19].C(=O)([O-])[O-].[K+].[K+].O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][C:16]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:17]=2[CH:18]=[O:19])[CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehydeHCID 10465267Methyl 3-hydroxy-4-methoxyphenylacetate

Product 1

HCID 58237485[3-(2-Formyl-4-trifluoromethyl-phenoxy)-4-methoxy-phenyl]-acetic acid methyl esterYield 23.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

(3-Hydroxy-4-methoxy-phenyl)-acetic acid methyl ester (1 g, 5.2 mmol), 2-fluoro-5-(trifluoromethyl)benzaldehyde (1 g, 5.2 mmol), and potassium carbonate (1.3 g, 10.4 mmol) were combined in THF (10 mL) and heated to 65° C. for 8 hours. After working-up the mixture with H2O and EtOAc, the crude material was purified by silica gel chromatography to give the desired product as a white solid (0.45 g).

Workup

  1. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4ff72c026e594f03a09b736ee0fbf1b3
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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