Lithium Hydroxide → Lithium (RS)-alpha-(Hydroxymethyl)-3,5-bis(trifluoromethyl)benzeneacetate

HRID 2212995Notes

Reaction equation

HRID 2212995 reaction equation
[OH-].[Li+:2].[OH:3][CH2:4][CH:5]([C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1)[C:6]([O:8]C)=[O:7].O1CCCC1>O.CO>[OH:3][CH2:4][CH:5]([C:10]1[CH:11]=[C:12]([C:20]([F:21])([F:23])[F:22])[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1)[C:6]([O-:8])=[O:7].[Li+:2]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 21955325(RS)-Methyl alpha-(Hydroxymethyl)-3,5-bis(trifluoromethyl)benzeneacetate

Product 1

HCID 86760236Lithium (RS)-alpha-(Hydroxymethyl)-3,5-bis(trifluoromethyl)benzeneacetateYield 176.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Lithium hydroxide (168 mg, 4 mmol) in water (2 mL) was added to a solution of (RS)-methyl α-(hydroxymethyl)-3,5-bis(trifluoromethyl)benzeneacetate (Description 7, 500 mg, 1.6 mmol) in methanol (4 mL). Methanol (2 mL) and tetrahydrofuran (2 mL) were added and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and the residue was dried azeotropically by evaporating toluene (×2) to to give the crude title compound as a colorless gum (870 mg), which was used without further purification. 1H NMR (400 MHz, CD3OD) δ 3.73–3.79 (1H, m), 3.85–3.92 (1H, m), 4.02–4.06 (1H, m), 7.80 (1H, s) and 7.98 (2H, s).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was dried azeotropically
  3. customby evaporating toluene (×2)

Sources & evidence

ORD record
ord-f2c5b4d84226488995abe2818aa3d800
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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