Lithium Hydroxide → HCID 58046316, compound

HRID 2359306Notes

Reaction equation

HRID 2359306 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[C:9]([CH2:17][O:18][CH3:19])[CH:8]=2)=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].[OH-].[Li+]>O1CCCC1.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[C:9]([CH2:17][O:18][CH3:19])[CH:8]=2)=[CH:4][C:3]=1[C:22]([F:23])([F:24])[F:25]

Participants

6

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 58046348Benzoic acid, 4-[4-chloro-3-(trifluoromethyl)phenoxy]-2-(methoxymethyl)-, methyl ester

Product 1

HCID 58046316HCID 58046316, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-[4-chloro-3-(trifluoromethyl)phenoxy]-2-(methoxymethyl)benzoate (Preparation 34, 0.140 g, 0.000374 mol) in tetrahydrofuran (3.00 mL) and water (3.00 mL) was added lithium hydroxide (0.050 g, 0.00209 mol) and the reaction stirred at room temperature under nitrogen for 2 hours. Then more lithium hydroxide (0.500 g, 0.0209 mol) was added and the reaction stirred at room temperature under nitrogen for 16 hours. The reaction was diluted with ethyl acetate (10.0 mL) and washed with water (10.0 mL). The organic layer was separated, dried with sodium sulphate, filtered and concentrated in vacuo to yield title compound as a pale yellow foam (0.134 g, 0.000374 mol, 99% yield).

Workup

  1. stirringthe reaction stirred at room temperature under nitrogen for 16 hours
  2. washwashed with water (10.0 mL)
  3. customThe organic layer was separated
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6436c74e9df845fcabe15a433073caf9
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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