Water → 4-(Ethoxymethyl)benzenemethanol

HRID 914481Notes

Reaction equation

HRID 914481 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][CH2:18][CH3:19])=[CH:12][CH:11]=1.O.[OH-].[Na+]>O1CCCC1>[CH2:18]([O:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=1)[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 28942624HCID 28942624, compound

Product 1

HCID 110301904-(Ethoxymethyl)benzenemethanolYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (0.39 g) was suspended in tetrahydrofuran (10 mL), a solution of 4-(ethoxymethyl)benzoic acid methyl ester (2.0 g) synthesized in Reference Example 38 in tetrahydrofuran (50 mL) was added under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was ice-cooled, and water (1.0 mL) and aqueous sodium hydroxide solution (1 mol/L, 4.0 mL) were successively added dropwise. After warming to room temperature, the mixture was stirred for 1 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (1.52 g) as a colorless oil.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooled
  4. temperatureAfter warming to room temperature
  5. stirringthe mixture was stirred for 1 hr
  6. filtrationThe reaction mixture was filtered through celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-30d3493434914ec5bb88e4d2b5a4abfd
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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