Water → 2-[4-(Hydroxymethyl)-2,6-dimethoxyphenoxy]ethan-1-ol

HRID 1925793Notes

Reaction equation

HRID 1925793 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([CH:14]=[O:15])=[CH:8][C:7]=1[O:16][CH3:17].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[OH:15][CH2:14][C:9]1[CH:10]=[C:11]([O:12][CH3:13])[C:6]([O:5][CH2:4][CH2:3][OH:2])=[C:7]([O:16][CH3:17])[CH:8]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 21226445Aluminium lithium hydrideHCID 43516604HCID 43516604, compound

Product 1

HCID 435167062-[4-(Hydroxymethyl)-2,6-dimethoxyphenoxy]ethan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-formyl-2,6-dimethoxyphenoxy)-acetate methyl ester (1.5 g, 5.9 mmol) in THF (30 mL, 0.2 M) was added LiAlH4 (403 mg, 10.6 mmol) at water temperature. The reaction mixture was stirred for 6 hours at room temperature, followed by addition of H2O, and then subjected to celite filtration. Evaporation of the resultant mixture under diminished pressure gave a white solid. Recrystallization of this solid from chloroform/hexane gave a colorless needle-like crystal (1.346 g, 100%, m.p. 26 to 28° C.).

Workup

  1. filtrationsubjected to celite filtration
  2. customEvaporation of the resultant mixture under diminished pressure
  3. customgave a white solid
  4. customRecrystallization of this solid from chloroform/hexane

Sources & evidence

ORD record
ord-c9f53b21075c4774b048a82be1ba3f8c
Source dataset
uspto-grants-2012_05
Patent number
US08178727B2

Reaction notes

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