Lithium hydroxide, monohydrate → HCID 68109007, compound

HRID 385106Notes

Reaction equation

HRID 385106 reaction equation
[CH2:1]([O:8][C:9]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]=1[O:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O>[CH2:1]([O:8][C:9]1[C:19]([C:20]([F:21])([F:22])[F:23])=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:24][CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68108366HCID 68108366, compound

Product 1

HCID 68109007HCID 68109007, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-benzyloxy-3-methoxy-5-trifluoromethylbenzoate (704 mg) was dissolved in tetrahydrofuran (6 mL) and water (2 mL), and lithium hydroxide monohydrate (333 mg) was added to the solution, and then the mixture was stirred at 60° C. for 3 hours. After the organic solvent was distilled off, the mixture was acidified with 1N hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (606 mg) as a colorless crystal.

Workup

  1. distillationAfter the organic solvent was distilled off
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5a88af4de9824ca991d71518d75d9327
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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