Aluminium lithium hydride → (3-Fluoro-5-methoxyphenyl)methanol

HRID 1522868Notes

Reaction equation

HRID 1522868 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:5](O)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 219424693-Fluoro-5-methoxybenzoic acid

Product 1

HCID 26985456(3-Fluoro-5-methoxyphenyl)methanolYield 104.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-fluoro-5-methoxybenzoic acid (5.1 g, 30 mmol) in dry ether at 0° C., LiAlH4 (3.44 g, 90 mmol) was added slowly. The reaction mixture was stirred at room temperature for 3 h, and quenched by slow addition of 1 M aqueous HCl solution (30 mL). The mixture was extracted with ethyl acetate (3×15 mL). The organic phase was dried over Na2SO4 and concentrated to give 4.9 g of (3-fluoro-5-methoxyphenyl)methanol. 1H NMR (CDCl3): δ 6.67-6.70 (m, 2H), 6.50-6.55 (m, 1H), 4.64 (d, 2H), 3.79 (s, 3H).

Workup

  1. customquenched by slow addition of 1 M aqueous HCl solution (30 mL)
  2. extractionThe mixture was extracted with ethyl acetate (3×15 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4a155a9c38a54806b62531613c39d484
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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