Aluminium lithium hydride → HCID 118307145, compound

HRID 921234Notes

Reaction equation

HRID 921234 reaction equation
[CH2:1]([C:4]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:5]=1[C:6](OC)=[O:7])[CH:2]=[CH2:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([C:4]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:5]=1[CH2:6][OH:7])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57443291HCID 57443291, compound

Product 1

HCID 118307145HCID 118307145, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 2-allyl-4-methylbenzoate (220 mg, 1.156 mmol) in THF (2 mL) was added LAH (2.313 mL, 2.313 mmol) and the reaction mixture was stirred at rt for 1 h. It was then added NH4Cl and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to isolate (2-allyl-4-methylphenyl)methanol (150 mg, 0.925 mmol, 80% yield) as an oil. 1H NMR (500 MHz, CDCl3) δ 7.31-7.25 (m, 1H), 7.10-7.03 (m, 2H), 6.03 (ddt, J=16.9, 10.4, 6.3 Hz, 1H), 5.13-5.00 (m, 2H), 4.69 (d, J=5.2 Hz, 2H), 3.48 (d, J=6.3 Hz, 2H), 2.36 (s, 3H), 1.53 (t, J=5.7 Hz, 1H).

Workup

  1. extractionadded NH4Cl and extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto obtain an oil, which
  6. customwas then purified by biotage
  7. washeluting with 10% EtOAc/hexane

Sources & evidence

ORD record
ord-78ce8f75f31c4a13b5b84eee6e22f15d
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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