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

HRID 379029Notes

Reaction equation

HRID 379029 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). Next, the aqueous layer was extracted with additional EtOAc (2×50 mL), the organic layers were combined, washed with brine, and dried (MgSO4). The title compounds was obtained by filtering and concentrating to dryness.

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. extractionNext, the aqueous layer was extracted with additional EtOAc (2×50 mL)
  6. washwashed with brine
  7. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-cfc0a830161845479db49df7ee137ff5
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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