Acetic Acid → HCID 18000323, compound

HRID 1653834Notes

Reaction equation

HRID 1653834 reaction equation
C(O)(=[O:3])C.[Cl:5][C:6]1[CH:24]=[CH:23][C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]=[C:18]([N+]([O-])=O)[CH3:19])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1.O.CO>[Fe].CCCCCC>[Cl:5][C:6]1[CH:24]=[CH:23][C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18](=[O:3])[CH3:19])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 53643148HCID 53643148, compound

Product 1

HCID 18000323HCID 18000323, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8058HexaneSolvent

Procedure

A mixture of 4-(4-chlorophenoxy)benzaldehyde (256 g) and butylamine (239 ml) in toluene (1 liter) was heated to reflux and the water formed removed through a Dean & Stark head. After 2 hr the mixture was concentrated in vacuo and the residue dissolved in acetic acid (750 ml) and nitroethane (118.5 ml), heated at 100° for 2 hr, cooled and poured into iced water. The yellow solid was filtered, dried in air and recyrstallised from ethanol (750 ml) to afford 4-(4-chlorophenoxy)phenyl-2-nitropropene (254.7 g), m.p. 69°-71°. Acetic acid (115 ml) was added over 30 min to a well stirred, refluxing mixture of the 4-(4-chlorophenoxy)phenyl-2-nitropropene (28.9 g), iron powder (56 g), water (20 ml) and methanol (150 ml). After 3 hr it was cooled and partitioned between water (500 ml) and dichloromethane (200 ml). The organic phase was filtered, washed with water and satd. aq. sodium bicarbonate, dried over magnesium sulphate and concentrated in vacuo to leave a yellow oil. Trituration with hexane afforded the title compound as fine colourless crystals (14.6 g), m.p. 50°-52°.

Workup

  1. temperaturerefluxing
  2. temperatureAfter 3 hr it was cooled
  3. custompartitioned between water (500 ml) and dichloromethane (200 ml)
  4. filtrationThe organic phase was filtered
  5. washwashed with water
  6. dry with materialaq. sodium bicarbonate, dried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customto leave a yellow oil

Sources & evidence

ORD record
ord-031257bda9024ebe9ac3e569c9b545ef
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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