Nitromethane → HCID 18971326, compound

HRID 2395256Notes

Reaction equation

HRID 2395256 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].N12CCCN=C1CCCCC2.[C:21](O)(=O)C=C.[N+:26](C)([O-:28])=[O:27]>>[N+:26]([CH:2]([CH2:3][CH3:21])[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])([O-:28])=[O:27]

Participants

5

Reactant 4

HCID 6375NitromethaneHCID 6581Acrylic AcidHCID 15458tert-Butyl acrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×

Product 1

HCID 18971326HCID 18971326, compound

Procedure

537 ml (3.7 mol) of tert-butyl acrylate were added dropwise, at a bath temperature of 70° C., to an initially introduced solution of 2.0 l of nitromethane and 7 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), with the pH, which could possibly have declined due to traces of acrylic acid, being maintained constant by the addition of appropriate quantities of DBU. After the exothermic reaction had subsided (rise of temperature to 90° C.), the mixture was allowed to cool for 60 min and then washed several times with dilute aqueous hydrochloric acid and water, dried and concentrated under reduced pressure, with 660 g of a reddish-brown oil remaining which was further purified by distillation (bp5 : 90° C.).

Workup

  1. customAfter the exothermic reaction
  2. custom(rise of temperature to 90° C.)
  3. temperatureto cool for 60 min
  4. washwashed several times with dilute aqueous hydrochloric acid and water
  5. customdried
  6. concentrationconcentrated under reduced pressure, with 660 g of a reddish-brown oil
  7. distillationwas further purified by distillation (bp5 : 90° C.)

Sources & evidence

ORD record
ord-9129251bfc9042cc965e8370d48a40b1
Source dataset
uspto-grants-1998_09
Patent number
US05814627

Reaction notes

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