Lithium borohydride → 2-Hydroxy-4-(hydroxymethyl)benzonitrile

HRID 379023Notes

Reaction equation

HRID 379023 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

HCID 4148881Lithium borohydrideHCID 16641129Methyl 4-cyano-3-hydroxybenzoate

Product 1

HCID 216969742-Hydroxy-4-(hydroxymethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. custompartitioned between EtOAc (50 mL) and 1N HCl (50 mL)
  5. extractionthe aqueous layer extracted with additional EtOAc (2×50 mL)
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. 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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