Water → (4-(2,2-Dimethoxyethyl)phenyl)methanol

HRID 2205696Notes

Reaction equation

HRID 2205696 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9](OC)=[O:10])=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Mg+2]>[CH3:16][O:15][CH:3]([O:2][CH3:1])[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86720817Methyl 4-(2,2-dimethoxyethyl)benzoate

Product 1

HCID 84773974(4-(2,2-Dimethoxyethyl)phenyl)methanolYield 62%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 24083Sulfuric acid magnesium salt (1:1)Solvent

Procedure

To a cooled (−78° C.) solution of methyl 4-(2,2-dimethoxyethyl)benzoate (assume 7.08 mmol) in THF (30 mL) was added drop wise a solution of lithium aluminium hydride (2.0 M in THF, 3.50 mL, 7.00 mmol). The reaction mixture was allowed to warm to RT over 4 hours. The mixture was sequentially treated with water (0.266 mL), 2M aqueous sodium hydroxide (0.266 mL) and water (3×0.266 mL). The mixture was diluted with ethyl acetate and magnesium sulfate added. The mixture was stirred at RT for 1 hour and then filtered through celite. The filter cake was washed with further ethyl acetate and the filtrates combined. The solvent was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane to afford the title compound (0.854 g, 62%).

Workup

  1. additionadded
  2. filtrationfiltered through celite
  3. washThe filter cake was washed with further ethyl acetate
  4. customThe solvent was evaporated at reduced pressure
  5. customthe residue was purified by flash column chromatography
  6. washeluting with 0-30% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-9c883fa22e8c4143b2260b17dd02849d
Source dataset
uspto-grants-2016_06
Patent number
US09371318B2

Reaction notes

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