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

HRID 337264Notes

Reaction equation

HRID 337264 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:17])=[C:8]([CH:14]=[CH:15][CH:16]=1)[C:9](OCC)=[O:10].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([CH3:17])=[C:8]([CH2:9][OH:10])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66959620Ethyl 3-(2,6-dimethylbenzyloxy)-2-methylbenzoate

Product 1

HCID 66959083(3-(2,6-Dimethylbenzyloxy)-2-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Ethyl 3-(2,6-dimethylbenzyloxy)-2-methylbenzoate (Step B, 5.94 g, 19.93 mmol) in dry THF (35 ml) was added drop wise LiAlH4 (1M in THF, 0.832 g, 21.92 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 0.1N HCl at 0° C., and 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 2:1) to give the title compound.

Workup

  1. customis consumed
  2. customquenched slowly with 0.1N HCl at 0° C.
  3. additionEtOAc (20 ml) was 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 2:1)

Sources & evidence

ORD record
ord-feafbc9bf0324af08446792181b8e243
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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