Iodine → 4-hydroxy-3-methoxy-2-nitrobenzonitrile

HRID 536228ノート

反応式

HRID 536228 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14].[OH-].[NH4+:16].II>C1COCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:16])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14]

参加物

5

反応物 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-

生成物 1

HCID 70592654-hydroxy-3-methoxy-2-nitrobenzonitrile収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-Hydroxy-3-methoxy-2-nitrobenzaldehyde (200 g, 1.01 mol) was dissolved in THF (2.5 L) and then ammonium hydroxide (2.5 L) was added followed by iodine (464 g, 1.8 mol). The resulting mixture was allowed to stir for 2 days at which time it was concentrated under reduced pressure. The residue was acidified with HCl (2 N) and extracted into diethyl ether. The organic layer was washed with brine and dried (sodium sulfate) and concentrated under reduced pressure. The residue was washed with diethyl ether and dried under vacuum to provide the title compound (166 g, 84%): 1H NMR (DMSO-d6) δ: 11.91 (1H, s), 7.67 (1H, d), 7.20 (1H, d), 3.88 (3H, s)

後処理

  1. concentrationwas concentrated under reduced pressure
  2. extractionextracted into diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with diethyl ether
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-041f6e276e7049b592989eb8f16fc7b0
出典データセット
uspto-grants-2014_10
特許番号
US08859572B2

反応ノート

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