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

HRID 480335Notes

Reaction equation

HRID 480335 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 H2and 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 H2and the product
  5. extractionwas 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-dc61aa0bc63a4d00be4ade5f5edd50fb
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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