Water → 5-Chloro-2-(hydroxymethyl)phenol

HRID 1006563Notes

Reaction equation

HRID 1006563 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:17]=[CH:16][C:11]([C:12](OC)=[O:13])=[C:10]([OH:18])[CH:9]=1.O>C1COCC1>[OH:13][CH2:12][C:11]1[CH:16]=[CH:17][C:8]([Cl:7])=[CH:9][C:10]=1[OH:18]

Participants

5

Reactant 3

HCID 962WaterHCID 327085Methyl 4-chloro-2-hydroxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 3271485-Chloro-2-(hydroxymethyl)phenolYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium aluminum hydride (1.1 g) in THF (50 ml), methyl 4-chloro-2-hydroxybenzoate (5.38 g; prepared in Reference Example 46.) in THF (50 ml) was added dropwise in a stream of argon at 0° C. After the solution was warmed to at room temperature, the solution was stirred for 30 minutes. To the reaction mixture, water was added. The mixture was extracted with mixture solution of ether-AcOEt, washed, dried over and concentrated under the reduced pressure. The residue was recrystallized from mixture solution of hexane-AcOEt to give the title compound (3.92 g) having the following physical data.

Workup

  1. extractionThe mixture was extracted with mixture solution of ether-AcOEt
  2. washwashed
  3. customdried over and
  4. concentrationconcentrated under the reduced pressure
  5. customThe residue was recrystallized from mixture solution of hexane-AcOEt

Sources & evidence

ORD record
ord-58e101d1045c46b491e231cf5a816c1c
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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