Water → 3-(Hydroxymethyl)-5-(methoxymethoxy)phenol

HRID 1678593Notes

Reaction equation

HRID 1678593 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH2:19][O:20][CH3:21])[CH:17]=1)[C:11](OC)=[O:12].O.[OH-].[Na+]>O1CCCC1>[OH:12][CH2:11][C:10]1[CH:9]=[C:8]([OH:7])[CH:17]=[C:16]([O:18][CH2:19][O:20][CH3:21])[CH:15]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23136427Methyl 3-hydroxy-5-(methoxymethoxy)benzoate

Product 1

HCID 231364173-(Hydroxymethyl)-5-(methoxymethoxy)phenolYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

With ice cooling, to a solution of aluminum lithium hydride (1.80 g, 47.5 mmol) in tetrahydrofuran (50 mL) was added dropwise a solution of methyl 3-hydroxy-5-(methoxymethoxy)benzoate (7.74 g, 36.5 mmol) in tetrahydrofuran (50 mL), and the mixture was stirred at room temperature for 4 hours. To the reaction solution were successively added water (2 mL), a 15% aqueous sodium hydroxide solution (2 mL) and water (7 mL), and the mixture was further stirred for 2 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=5:5) to give the title compound (4.46 g, yield 66%) as an oily matter.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=5:5)

Sources & evidence

ORD record
ord-1d2da87974e544d585c43681b0dfbd3a
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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