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

HRID 1421751Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[C:6]([OH:12])[CH:5]=1.[Li+].[BH4-]>C1COCC1>[OH:12][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][C:7]=1[C:10]#[N:11]

Participants

Conditions

Temperature: 70 °C

Procedure

4-cyano-3-hydroxybenzoic acid methyl ester, Example 34, Step 3 (2.5 g, 14 mmol) was dissolved in THF (70 ml). LiBH4 in THF (2 M, 14 ml, 28 mmol) was added. The reaction mixture was heated to 70° C. for 60 hrs. The reaction mixture was quenched carefully with 3N HCl. The solvent was removed in vacuo and the crude material was purified by flash chromatography [10% MeOH(5% NH4OH)/CH2Cl2 ] to yield the desired product.

Workup

customThe reaction mixture was quenched carefully with 3N HCl
customThe solvent was removed in vacuo
customthe crude material was purified by flash chromatography [10% MeOH(5% NH4OH)/CH2Cl2 ]

Sources & evidence

ORD record: ord-5df9c3a0480542939d8bfcb2360619e8
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06077853

Reaction notes

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