2-Fluoro-3-methoxybenzoic acid → 2-Fluoro-3-methoxybenzyl alcohol
Reaction equation
[F:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[F:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][OH:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a mixture of 2-fluoro-3-methoxybenzoic acid (14.5 g, 85.2 mmol) in dry ethyl ether (300 mL) at 0° C., LiAlH4 (9.3 g, 245 mmol) was added over a 20 min period. The resulting mixture was heated at 80° C. for 20 min and then stirred at room temperature for 1 h. The mixture was carefully quenched with 15% NaOH (10 mL) at 0° C., and water (100 mL) was added. The mixture was extracted with ethyl acetate (3×100 mL), and the combined organic layers were dried (Na2SO4) and concentrated in vacuo to give the title compound (13.5 g).
Workup
- customThe mixture was carefully quenched with 15% NaOH (10 mL) at 0° C.
- additionwater (100 mL) was added
- extractionThe mixture was extracted with ethyl acetate (3×100 mL)
- dry with materialthe combined organic layers were dried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-cb370e9d6c9546ad9c7e381b10437735
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703810B2
Reaction notes
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