Water → HCID 19004407, compound

HRID 1929628Notes

Reaction equation

HRID 1929628 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1.O.[OH-].[Na+]>C1COCC1>[F:19][C:18]([F:20])([F:21])[C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH2:9][OH:8])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 28829557HCID 28829557, compound

Product 1

HCID 19004407HCID 19004407, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cooled suspension of lithium aluminum hydride (0.972 g; 25.622 mmol) in anhydrous THF (60 ml) was added dropwise a solution of (4-trifluoromethyl-phenoxy)-acetic acid methyl ester (3.000 g; 12.811 mmol) in anhydrous THF (40 ml). The resulting reaction mixture was further stirred at 0° C. for 20 min. Water (1 ml), 15% aq. NaOH (1 ml), and water (3 ml) were then successively added dropwise. Filtration, concentration to dryness under reduced pressure, and purification by FC (DCM/MeOH, 19/1) afforded 2-(4-trifluoromethyl-phenoxy)-ethanol as a colorless solid (2.370 g; 90%). LC-MS: tR=0.84 min.; [M+H]+: no ionisation.

Workup

  1. customThe resulting reaction mixture
  2. filtrationFiltration, concentration to dryness
  3. customunder reduced pressure, and purification by FC (DCM/MeOH, 19/1)

Sources & evidence

ORD record
ord-ac16930fa2be47d0bda01d1d62440fe6
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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