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

HRID 1421723Notes

Reaction equation

HRID 1421723 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 (2.0 M 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-2e70a119170048dbb0b88789dbd240ff
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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