Aluminium lithium hydride → 2-Chloro-4-(hydroxymethyl)-5-methoxyphenol

HRID 630398Notes

Reaction equation

HRID 630398 reaction equation
[Cl:1][C:2]1[C:3]([OH:14])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:11]=[C:6]([CH2:7][OH:8])[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[OH:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21536136Benzoic acid, 5-chloro-4-hydroxy-2-methoxy-, methyl ester2×

Product 1

HCID 671453092-Chloro-4-(hydroxymethyl)-5-methoxyphenolYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 5-chloro-4-hydroxy-2-methoxybenzoate (intermediate 53; 204 mg; 0.94 mmol) in 4.6 ml of anhydrous THF was stirred with external ice/water bath cooling. A solution of 1M LiAlH4 in THF was dropped in (1.9 ml; 1.9 mmol). After 5 minutes the external bath was removed and the stirring prosecuted for 3 additional hours. With external cooling 0.072 ml of water were added followed by 0.072 ml of 4N NaOH solution and 0.144 additional ml of water. After filtration the cake was thoroughly washed with THF and the filtrates were concentrated giving the title compound in 34% yield.

Workup

  1. temperaturecooling
  2. customAfter 5 minutes the external bath was removed
  3. temperatureWith external cooling 0.072 ml of water
  4. additionwere added
  5. filtrationAfter filtration the cake
  6. washwas thoroughly washed with THF
  7. concentrationthe filtrates were concentrated

Sources & evidence

ORD record
ord-be4881ac89084a83aa7705c9f3def052
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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