Aluminium lithium hydride → [4-(4-Fluorophenoxy)phenyl]methanol

HRID 1741004Notes

Reaction equation

HRID 1741004 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:25]=[CH:24][C:11]([O:12][C:13]2[CH:23]=[CH:22][C:16]([C:17](OCC)=[O:18])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1>C(OCC)C>[F:7][C:8]1[CH:25]=[CH:24][C:11]([O:12][C:13]2[CH:23]=[CH:22][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 21834365Ethyl 4-(4-fluorophenoxy)benzoate

Product 1

HCID 22293127[4-(4-Fluorophenoxy)phenyl]methanolYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (0.25 g, 6.69 mmol) was slurried in 20 ml of dry diethyl ether and cooled in an ice bath. The ethyl 4-(4-fluorophenoxy)benzoate (2.32 g, 8.91 mmol) in 5 ml of dry diethyl ether was added dropwise and the reaction was stirred at room temperature overnight. More lithium aluminum hydride (0.25 g) was added and the reaction was stirred for four hours. The reaction was carefully quenched by sequential addition of 0.5 ml of water, 0.5 ml of 15% NaOH solution in water, and 1.5 ml of water. The resulting white precipitate was filtered using celite and washed with diethyl ether and discarded. The filtrate and washings were combined and concentrated to afford 1.92 g (99%) of the subtitle compound.

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe reaction was stirred for four hours
  3. customThe reaction was carefully quenched by sequential addition of 0.5 ml of water, 0.5 ml of 15% NaOH solution in water, and 1.5 ml of water
  4. filtrationThe resulting white precipitate was filtered
  5. washwashed with diethyl ether
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be17f2979abb474f8ea3e05fc648348f
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

Loading…