Methyl iodide → HCID 20439310, compound

HRID 1995885Notes

Reaction equation

HRID 1995885 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]#[N:13])[CH2:4][CH2:3]1.[CH3:15]I>C(O)(C)(C)C>[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:15])([C:12]#[N:13])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 1741091-Naphthalenecarbonitrile, 1,2,3,4-tetrahydro-4,4-dimethyl-

Product 1

HCID 20439310HCID 20439310, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

81.5 g of 1,1-dimethyl-4-cyano-tetralin are added dropwise to 49 g of potassium tert.butylate in 400 ml of tert.butanol and the mixture is stirred at room temperature for 1 hour. At 5° C. there are then added dropwise 72 g of methyl iodide and the mixture is stirred for 15 hours without cooling. The bulk of the tert.butanol is distilled off, the residue is taken up in ether and washed neutral with water, dried over sodium sulphate and evaporated. The residue is distilled in vacuo and there are obtained 61 g of 1,1,4-trimethyl-4-cyano-tetralin of boiling point 85° C./0.25 mmHg; melting point 46° C.; yield 70%. Odour: resembling (3), but more intensive, woody.

Workup

  1. stirringthe mixture is stirred for 15 hours
  2. temperaturewithout cooling
  3. distillationThe bulk of the tert.butanol is distilled off
  4. washwashed neutral with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. distillationThe residue is distilled in vacuo and there

Sources & evidence

ORD record
ord-3c173191e7a44f04872f9e0a78d69802
Source dataset
uspto-grants-1983_09
Patent number
US04406828

Reaction notes

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