Aluminium lithium hydride → (3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)methanol

HRID 1958844Notes

Reaction equation

HRID 1958844 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:9](OCC)=[O:10].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:2]([CH3:1])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66692649Ethyl 3-(2,6-dimethylbenzyloxy)-4-methoxybenzoate

Product 1

HCID 66959381(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Ethyl 3-(2,6-dimethylbenzyloxy)-4-methoxybenzoate (Step B, 6.04 g, 19.23 mmol) in dry THF (30 ml) was added drop wise LiAlH4 (1M in THF, 0.803 g, 21.16 mmol) at 0° C. under argon. The reaction mixture was stirred for 4 hours or until all the starting material is consumed, then quenched slowly with 1N HCl, EtOAc (20 ml) was added to the reaction mixture. The reaction mixture was filtered and precipitate was washed with EtOAc (25 ml×2). The combined organic layer was washed with 0.1N HCl, brine, dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1) to give the title compound.

Workup

  1. customis consumed
  2. customquenched slowly with 1N HCl, EtOAc (20 ml)
  3. additionwas added to the reaction mixture
  4. filtrationThe reaction mixture was filtered
  5. washprecipitate was washed with EtOAc (25 ml×2)
  6. washThe combined organic layer was washed with 0.1N HCl, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography on a silica gel column (hex:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-ac2b4bf807dc4ed28a98e138cc41123d
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

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