Water → [4-Fluoro-3-[(4-fluorophenyl)methoxy]phenyl]methanol

HRID 514527Notes

Reaction equation

HRID 514527 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86725638Methyl 4-fluoro-3-[(4-fluorophenyl)methoxy]benzoate

Product 1

HCID 86725639[4-Fluoro-3-[(4-fluorophenyl)methoxy]phenyl]methanolYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-fluoro-3-[(4-fluorophenyl)methoxy]benzoate (571 mg, 2.05 mmol) in THF (6 mL) cooled to −50° C., was added LiAlH4 solution (4.6 mL, 4.11 mmol, 1.0 M in THF) drop wise. Thereto, the mixture was stirred at this temperature for 1 h. Added water (0.2 mL) slowly, followed by NaOH (aq, 10%, 0.2 mL) and water (0.6 mL), the resulting mixture was filtered and washed with THF, the filtrate was concentrated to give 444 mg of the title compound (86%). 1H NMR (400 MHz, CDCl3): δ 1.67 (1H, t, J=6.0 Hz), 4.62 (2H, d, J=6.0 Hz), 5.10 2H, s), 6.87-6.91 (1H, m), 7.04-7.09 (4H, m), 7.40-7.43 (2H, m).

Workup

  1. filtrationthe resulting mixture was filtered
  2. washwashed with THF
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b97768d04ec945eba76d65e3e2baa164
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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