Benzoic Acid → 5-Nitrocyclohex-1-ene-1-carbaldehyde

HRID 1918275Notes

Reaction equation

HRID 1918275 reaction equation
[N+:1]([CH:4]([CH2:9][CH2:10][CH:11]=O)[CH2:5][CH2:6][CH:7]=[O:8])([O-:3])=[O:2].N1CCCC1.C(O)(=O)C1C=CC=CC=1>C(Cl)Cl>[N+:1]([CH:4]1[CH2:5][C:6]([CH:7]=[O:8])=[CH:11][CH2:10][CH2:9]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 31268PyrrolidineHCID 109429314-nitroheptanedial

Product 1

HCID 575067495-Nitrocyclohex-1-ene-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-Nitro-heptanedial (35.2 g, 0.2 mol) in methylene chloride (0.7 L) were added pyrrolidine (2 ml, 0.024 mol) and benzoic acid (1.46 g, 0.012 mol), and the resulting mixture was refluxed for 10 to 15 hours. The reaction mixture was cooled to room temperature, washed with 1N HCl (170 ml), saturated with NaHCO3 (170 ml) and water (170 ml) and concentrated to give brownish oil with a purity of about 80%. The product was carried to the next step without further purification. Yield: 32.2 g, 75%. 1H NMR (400 MHz, CDCl3) d 2.29-2.34 (m, 2H), 2.46-2.64 (m, 2H), 2.85-2.88 (m, 2H), 4.74 (m, 1H), 6.86 (m, 1H), 9.50 (s, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for 10 to 15 hours
  2. washwashed with 1N HCl (170 ml), saturated with NaHCO3 (170 ml) and water (170 ml)
  3. concentrationconcentrated
  4. customto give brownish oil with a purity of about 80%
  5. customThe product was carried to the next step without further purification

Sources & evidence

ORD record
ord-7dbbb0450af2408ab01192cfb5d2a7e0
Source dataset
uspto-grants-2013_12
Patent number
US08618314B2

Reaction notes

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