Water → 2,4,6-Trichlorobenzyl alcohol

HRID 2289420Notes

Reaction equation

HRID 2289420 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:9]=1[C:10](Cl)=[O:11].O.[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]([Cl:18])[C:9]=1[CH2:10][OH:11]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 45825742,4,6-Trichlorobenzyl alcoholYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminium hydride (1M in THF, 18 mmol, 18 ml) was added slowly to a solution of 2,4,6-trichlorobenzoyl chloride (4.35 g, 17.8 mmol) in THF (70 ml) at 0°. After 1 h water (685 μl) was added, followed by aqueous sodium hydroxide (3M, 685 μl) and more water (2.06 ml). The suspension was stirred vigorously for 1 h, the precipitate filtered off and the filtrate evaporated in vacuo to give a slightly yellow solid. Recrystallisation from diisopropylether gave the title compound as white needles (2.63 g, 70%), m.p. 100-101°δH (CDCl3) 7.35 (2H, s, ArH), 4.91 (2H, br s, CH2CH) and 2.07 (1H, br s, CH); m/z (ES, 60V) 193 (M--OH).

Workup

  1. filtrationthe precipitate filtered off
  2. customthe filtrate evaporated in vacuo
  3. customto give a slightly yellow solid
  4. customRecrystallisation from diisopropylether

Sources & evidence

ORD record
ord-97cda0bb36674b39b79e46e58c22e705
Source dataset
uspto-grants-2000_07
Patent number
US06093696

Reaction notes

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