Hydrochloric Acid → 2-Hydroxy-4-(hydroxymethyl)benzonitrile

HRID 1585901Notes

Reaction equation

HRID 1585901 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[C:5](O)[CH:4]=1)#[N:2].[Li+].[BH4-].Cl.C1C[O:20]CC1>>[OH:8][CH2:7][C:6]1[CH:11]=[CH:12][C:3]([C:1]#[N:2])=[C:4]([OH:20])[CH:5]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 22616130Methyl 4-cyano-2-hydroxybenzoate

Product 1

HCID 216969742-Hydroxy-4-(hydroxymethyl)benzonitrile

Procedure

Methyl 4-cyano-2-hydroxybenzoate (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 for 18 hr. The reaction mixture was cooled to room temperature, poured into 1N HCl solution and extracted with EtOAc (2×). Organics combined and dried (MgSO4), filtered and concentrated to dryness to give the title compound which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hr
  3. extractionextracted with EtOAc (2×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9973e2b6f54446bb8ef6fc4a7f12d1a2
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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