Benzyl Alcohol → Benzonitrile, 4-(hydroxymethyl)-3-methoxy-

HRID 882857ノート

反応式

HRID 882857 の反応式
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([Cu])#[N:10].C[CH2:13][O:14]C(C)=O.[NH4+].[Cl-].[NH4+].[OH-]>CN(C=O)C>[OH:8][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:9]#[N:10])=[CH:4][C:3]=1[O:14][CH3:13]

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 21863491Ammonium chloride ammonium hydroxideHCID 178418546HCID 178418546、化合物

生成物 1

HCID 53997281Benzonitrile, 4-(hydroxymethyl)-3-methoxy-

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

To the benzyl alcohol prepared in step 1 (0.86 g, 4.0 mmol) in DMF (8 mL) was added CuCN (1.1 g, 12 mmol). The mixture was warmed to 150° C. and stirred for 20 h. The mixture was then cooled to room temperature and EtOAc was added, followed by a saturated NH4Cl/NH4OH solution. The mixture was stirred vigorously for 10 minutes and extracted with EtOAc, then the organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography provided 4-hydroxymethyl-3-methoxy-benzonitrile (0.38 g, 2.3 mmol).

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. stirringThe mixture was stirred vigorously for 10 minutes
  3. extractionextracted with EtOAc
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-280f73ee025941259dcc9f362a987777
出典データセット
uspto-grants-2012_08
特許番号
US08236805B2

反応ノート

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