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

HRID 882857노트

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HRID 882857 반응식
[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]

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 21863491Ammonium chloride ammonium hydroxideHCID 178418546HCID 178418546, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-280f73ee025941259dcc9f362a987777
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236805B2

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