Aluminium lithium hydride → HCID 86723756, compound

HRID 577528Notes

Reaction equation

HRID 577528 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[C:10]([O:19][CH:20]([CH3:22])[CH3:21])[C:11]([CH3:18])=[C:12]([CH:17]=1)[C:13](OC)=[O:14]>C1COCC1>[Br:7][C:8]1[CH:9]=[C:10]([O:19][CH:20]([CH3:22])[CH3:21])[C:11]([CH3:18])=[C:12]([CH2:13][OH:14])[CH:17]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86723757HCID 86723757, compound

Product 1

HCID 86723756HCID 86723756, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (1.90 g, 50.2 mmol) in dry THF (60 mL) was added dropwise methyl 5-bromo-2-methyl-3-(propan-2-yloxy)benzoate (Cpd PP, 17.0 g, 65.6 mmol) in THF (40 mL) at −5° C. After the addition, the resulting mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was quenched with 20% NaOH (10 mL) at −5° C. and then stirred at room temperature for 30 minutes. The resulting mixture was filtered and the solids were washed with EtOAc (3×30 mL). The filtrate was concentrated under vacuum to give [5-bromo-2-methyl-3-(propan-2-yloxy)phenyl]methanol (108a, 8 g, 74%) as a yellow oil.

Workup

  1. additionAfter the addition
  2. customThe reaction mixture was quenched with 20% NaOH (10 mL) at −5° C.
  3. stirringstirred at room temperature for 30 minutes
  4. filtrationThe resulting mixture was filtered
  5. washthe solids were washed with EtOAc (3×30 mL)
  6. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-6d13906fa4d14e12841d015a48e9e71c
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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