Aluminium lithium hydride → (3-TERT-BUTOXY-PHENYL)-METHANOL

HRID 413428Notes

Reaction equation

HRID 413428 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:12]=1)C>C(OCC)C>[C:18]([O:17][C:13]1[CH:12]=[C:11]([CH2:10][OH:9])[CH:16]=[CH:15][CH:14]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22261682HCID 22261682, compound

Product 1

HCID 23269370(3-TERT-BUTOXY-PHENYL)-METHANOLYield 91.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of LiAlH4 (1.707 g, 0.045 mol) in anhydrous diethyl ether (80 mL) in a 3-necked rb flask equipped with addition funnel at 0° C. in an ice-water bath was added dropwise a solution of 3-tert-butoxy-benzoic acid ethyl ester (5.0 g, 0.0225 mol) in ether (20 mL). The reaction mixture was left to warm to rt over 15 min, then cooled in an ice-water bath and quenched by dropwise addition of H2O. The mixture was partitioned between ether and H2O, the aqueous layer washed with ether (2×30 mL), the organics combined, washed with brine, dried (MgSO4), filtered and concentrated to give 3.70 g (82%) of the title compound.

Workup

  1. customequipped with addition funnel at 0° C. in an ice-water bath
  2. waitThe reaction mixture was left
  3. temperaturecooled in an ice-water bath
  4. customquenched by dropwise addition of H2O
  5. customThe mixture was partitioned between ether and H2O
  6. washthe aqueous layer washed with ether (2×30 mL)
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-7e1c24323daa4394ab603619b7d8375b
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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