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

HRID 2382169ノート

反応式

HRID 2382169 の反応式
[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]

参加物

5

反応物 3

HCID 243Benzoic AcidHCID 31268PyrrolidineHCID 109429314-nitroheptanedial

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5dba287d049f4d4bb387211c5310e66b
出典データセット
uspto-grants-2012_09
特許番号
US08258319B2

反応ノート

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