Water → HCID 89619306, compound

HRID 1525668Notes

Reaction equation

HRID 1525668 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH2:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].O.[OH-].[Na+]>CO.CCOC(C)=O.Cl>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:17][CH:18]=2)=[CH:4][C:3]=1[C:21]([F:22])([F:23])[F:24]

Participants

7

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 89619235HCID 89619235, compound

Product 1

HCID 89619306HCID 89619306, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of ethyl 4-{[4-chloro-3-(trifluoromethyl)phenoxy]methyl}benzoate (Preparation 17, 350 mg, 0.98 mmol) in methanol (8.0 mL) was added water (2 mL) followed by sodium hydroxide (400 mg, 9.8 mmol). The reaction mixture was heated to 55° C. for 3 hours, then cooled and diluted with EtOAc (50 mL) and 2M HCl (50 mL). The aqueous layer was separated and washed with EtOAc (2×50 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to yield a white solid as the title compound (276 mg, 86%).

Workup

  1. temperaturecooled
  2. customThe aqueous layer was separated
  3. washwashed with EtOAc (2×50 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d3bfa579ed84828a67becd97ac7f9f3
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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