Formic Acid → Ethyl 2-(3-formylphenyl)acetate

HRID 2298197Notes

Reaction equation

HRID 2298197 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#N)[CH:7]=1)[CH3:2].C(O)=[O:16]>[Al].[Ni]>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]=[O:16])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 11194802Ethyl 2-(3-cyanophenyl)acetate

Product 1

HCID 23076590Ethyl 2-(3-formylphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6336846Nickel aluminideCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of (3-cyano-phenyl)-acetic Acid ethyl ester (4.8 g, 25.4 mmol) in 75% aqueous formic Acid was added nickel-aluminum alloy (4.6 g). The mixture was heated at reflux (100° C.) for 2.25 h. The reaction mixture was cooled and was filtered through Celite with the aid of boiling EtOH. The filtrate was diluted with H2O and the product was extracted into CHCl3 (3×). The organic solution was stirred with saturated NaHCO3 solution until a pH of 8 was attained. The organic solution was dried over MgSO4, filtered, and concentrated. The product was purified by flash chromatography (5:1 hexanes/EtOAc) to afford the title compound (3.33 g). 1H NMR (400 MHz, CDCl3) δ 7.76-7.79 (m, 2H), 7.47-7.57 (m, 2H), 4.15 (q, 2H), 3.69 (s, 2H), 1.25 (t, 3H); MS 193 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. filtrationwas filtered through Celite with the aid of boiling EtOH
  4. additionThe filtrate was diluted with H2O
  5. extractionthe product was extracted into CHCl3 (3×)
  6. dry with materialThe organic solution was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe product was purified by flash chromatography (5:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-50168d188b2c48998afe2c09dd22385c
Source dataset
uspto-grants-2002_12
Patent number
US06492412B2

Reaction notes

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