Ethanol → 2,3,5,6-Tetrafluorobenzyl alcohol

HRID 1995688

Reaction equation

HRID 1995688 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[C:16]([F:17])=[CH:15][C:14]([F:18])=[C:13]([F:19])[C:9]=1[C:10](O)=[O:11].C(O)C.O>CCOCC>[F:7][C:8]1[C:16]([F:17])=[CH:15][C:14]([F:18])=[C:13]([F:19])[C:9]=1[CH2:10][OH:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 5675332,3,5,6-Tetrafluorobenzoic AcidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 27340292,3,5,6-Tetrafluorobenzyl alcoholYield 46.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminium hydride (4.6 g) was added in small portions to a stirred solution of 2,3,5,6-tetrafluorobenzoic acid (30.0 g) in dry ether (600 ml) at the ambient temperature, and stirring continued for a period of 3 hours. After decomposition of the excess lithium aluminium hydride with ethyl alcohol, water was added in excess and the ethereal phase separated, washed with water, and concentrated to yield crude 2,3,5,6-tetrafluorobenzyl alcohol (13.0 g) as a colourless oil.

Workup

  1. customseparated
  2. washwashed with water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d48cfcf8ff0740429f24171d1e57a511
Source dataset
uspto-grants-1983_09
Patent number
US04405640

Linked notes

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