Formic Acid → HCID 86598751, compound

HRID 2104552Notes

Reaction equation

HRID 2104552 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#N)=[CH:9][CH:8]=1)=[O:6])[CH3:2].C(O)=[O:17]>[Ni]>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[O:17])=[CH:9][CH:8]=1)[OH:6])[CH3:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 4065229Ethyl 4-cyanobenzoylformate

Product 1

HCID 86598751HCID 86598751, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A mixture of (4-cyano-phenyl)-oxo-acetic acid ethyl ester 0.41 g, 2.0 mmol) in 25 mL of 90% formic acid and a large excess of Raney nickel (50% slurry in water) was refluxed for 1 hr. The solid was filtered off and the liquid was concentrated. The crude material was purified by silica gel chromatography (5˜100% ethyl acetate/hexane) to give 0.35 g of (4-formyl-phenyl)-hydroxy-acetic acid ethyl ester as an oil.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe liquid was concentrated
  3. customThe crude material was purified by silica gel chromatography (5˜100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e218d1d3dd8848fbab48e4f19d03e39a
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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