Aluminium lithium hydride → HCID 60026402, compound

HRID 400636Notes

Reaction equation

HRID 400636 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][C:16](=[O:21])[CH2:15][C:14]2([CH3:23])[CH3:22])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[C:7]([C:11]1[CH:20]=[CH:19][C:18]([OH:17])=[C:13]([C:14]([CH3:23])([CH3:22])[CH2:15][CH2:16][OH:21])[CH:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 60026719HCID 60026719, compound

Product 1

HCID 60026402HCID 60026402, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled suspension of 1.99 g of LAH in 60 mL of THF at 0° C. was added a solution of 6-tert-butyl-4,4-dimethylchroman-2-one (8.1 g, 34.9 mmol) in 10 mL of THF by addition funnel. The reaction mixture was warmed to room temperature and stirred until TLC indicated the reaction was complete. After 1 hour, the reaction mixture was cooled in ice bath and carefully quenched with a minimum amount of water. The reaction mixture was then dried over magnesium sulfate and filtered through diatomaceous earth. The filtrate was concentrated in vacuo, the residue was taken up in hexanes, and the solids isolated by filtration to afford 5 g of 4-tert-butyl-2-(3-hydroxy-1,1-dimethylpropyl)phenol.

Workup

  1. additionby addition funnel
  2. temperaturethe reaction mixture was cooled in ice bath
  3. customcarefully quenched with a minimum amount of water
  4. dry with materialThe reaction mixture was then dried over magnesium sulfate
  5. filtrationfiltered through diatomaceous earth
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe solids isolated by filtration

Sources & evidence

ORD record
ord-9c3cbb15557f4b85a0edaf23a7f493a9
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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