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

HRID 882857Notes

Reaction equation

HRID 882857 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-280f73ee025941259dcc9f362a987777
Source dataset
uspto-grants-2012_08
Patent number
US08236805B2

Reaction notes

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