Lithium borohydride → 2-Hydroxy-4-(hydroxymethyl)benzonitrile
Reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][C:4]=1[OH:13])#[N:2].[Li+].[BH4-]>C1COCC1>[OH:13][C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=[CH:12][C:3]=1[C:1]#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 4-cyano-3-hydroxybenzoate (as described in Example 4, Step C) (0.50 g, 2.82 mmol) was dissolved in dry THF (30 mL), treated with LiBH4 (2.0M solution in THF) (5.64 mL, 11.28 mmol) and heated at reflux overnight. The reaction mixture was concentrated, then partitioned between EtOAc (50 mL) and 1N HCl (50 mL), the aqueous layer extracted with additional EtOAc (2×50 mL), the organic layers combined, washed with brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound.
Workup
- temperatureheated
- temperatureat reflux overnight
- concentrationThe reaction mixture was concentrated
- custompartitioned between EtOAc (50 mL) and 1N HCl (50 mL)
- extractionthe aqueous layer extracted with additional EtOAc (2×50 mL)
- washwashed with brine
- dry with materialdried (MgSO4)
- filtrationFiltration and concentration to dryness
Sources & evidence
- ORD record
- ord-497a60a86f564e3fa86a9fae5b2803ed
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297239B1
Reaction notes
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