Methyl iodide → HCID 10330141, compound

HRID 1288276Notes

Reaction equation

HRID 1288276 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([OH:13])=[C:9]([CH:12]=1)[C:10]#[N:11])([CH3:4])([CH3:3])[CH3:2].[Na].[CH3:15]I>C(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:13][CH3:15])=[C:9]([CH:12]=1)[C:10]#[N:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 5360545SodiumHCID 21504498HCID 21504498, compound

Product 1

HCID 10330141HCID 10330141, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-tert-Butyl-2-hydroxybenzonitrile (50 g; prepared as described by F. B. Dains and I. R. Rothrock, J. Amer. Chem., 1894 16, 635) was added to a solution of sodium (7.43 g.) in anhydrous ethanol (150 ml.), followed by methyl iodide (50 ml.). The mixture was refluxed for 3 hours, during which time a further quantity of methyl iodide (20 ml.) was added in portions. The mixture was evaporated in vacuo, and the residue treated with water (500 ml.). The oil obtained was extracted with diethyl ether, and the aqueous layer further extracted twice with diethyl ether. The combined extracts were dried and evaporated, and the residual oil was distilled in vacuo to give 5-tert-butyl-2-methoxybenzonitrile (50.3 g.), b.p. 138°-140° C./0.2 mm.Hg.

Workup

  1. additionwas added in portions
  2. customThe mixture was evaporated in vacuo
  3. additionthe residue treated with water (500 ml.)
  4. customThe oil obtained
  5. extractionwas extracted with diethyl ether
  6. extractionthe aqueous layer further extracted twice with diethyl ether
  7. customThe combined extracts were dried
  8. customevaporated
  9. distillationthe residual oil was distilled in vacuo

Sources & evidence

ORD record
ord-e13b67139659496eba372d3d51057eae
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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