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

HRID 885402Notes

Reaction equation

HRID 885402 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[CH:22](OC)[O:23]C)[CH:6]=1.Cl>C1COCC1>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][C:13]=2[CH:22]=[O:23])[CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 58237632[3-(2-Dimethoxymethyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester

Product 1

HCID 58237636[3-(2-Formyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl esterYield 113.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To [3-(2-dimethoxymethyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester (0.479 g, 1.2 mmol) in THF (4 mL) was added hydrogen chloride (4N in 1,4-dioxane; 1.5 mL), and the reaction was stirred at 70° C. for 1.5 hours. Additional HCl (0.5 mL) was added, and the reaction was stirred for 40 minutes at 70° C. The mixture was partitioned between H2O and EtOAc, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried and concentrated to give the desired product (0.46 g).

Workup

  1. stirringthe reaction was stirred for 40 minutes at 70° C
  2. customThe mixture was partitioned between H2O and EtOAc
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. customThe combined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8013f8796dd7464b96e513ef9d2267fd
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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