Hydrochloric Acid → HCID 67441634, compound

HRID 1667644Notes

Reaction equation

HRID 1667644 reaction equation
[C:1]([C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)=[CH:12][C:11]=2/[CH:27]=[CH:28]\[C:29]([O:31]C)=[O:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+].Cl>O1CCCC1>[C:1]([C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:18][CH:17]=3)=[CH:12][C:11]=2/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58007941HCID 58007941, compound

Product 1

HCID 67441634HCID 67441634, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl (Z)-3-{4-[4-(tert-butyl)phenoxy]-4′-(trifluoromethoxy)biphenyl-3-yl}propenoate (590 mg, 1.293 mmol), methanol (1 ml), tetrahydrofuran (4 ml) and 2N aqueous sodium hydroxide (1.94 ml) was stirred at 60° C. for 1 hour. The reaction mixture was cooled to room temperature, acidified by addition of 2N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (550 mg, 93.2%) as a pale yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-27e0e2810aee4e9796ecff5a9f3dc370
Source dataset
uspto-grants-2011_10
Patent number
US08044236B2

Reaction notes

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