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

HRID 1969040Notes

Reaction equation

HRID 1969040 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.CCOC(C)=O.O>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

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 8857Ethyl AcetateHCID 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 ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

[3-(2-Dimethoxymethyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester (0.479 g, 1.42 mmol) and hydrogen chloride (4N in 1,4-dioxane; 1.5 mL, 6.0 mmol) were combined in THF (4 mL) and stirred at 70° C. for 1 hour. Some starting material was still seen by analytical LCMS, so additional hydrogen chloride (4N in 1,4-dioxane; 0.5 mL) was added, and the reaction was stirred for another hour at 70° C. After cooling to room temperature, the mixture was worked up with EtOAc and H2O, and the combined organic layers were dried and concentrated to give the title compound.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred for another hour at 70° C
  3. temperatureAfter cooling to room temperature
  4. customthe combined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-63b98c6bcc824c08a43cf9e05ff07a0d
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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