Methyl iodide → HCID 20439309, compound

HRID 1995886Notes

Reaction equation

HRID 1995886 reaction equation
[CH3:1][C:2]1([CH3:16])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:4][CH2:3]1.[CH3:17]I>C(O)(C)(C)C>[CH3:16][C:2]1([CH3:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:17])([C:12](=[O:15])[CH2:13][CH3:14])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 1664451-(1,2,3,4-Tetrahydro-4,4-dimethyl-1-naphthalenyl)-1-propanone

Product 1

HCID 20439309HCID 20439309, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
5 °C

Procedure

5.6 g of potassium tert.butylate are placed in 42.5 ml of tert.butanol and 10.8 g of 1,1-dimethyl-4-propionyl-tetralin are added dropwise thereto. The mixture is stirred for 1 hour, cooled to 5° C. and 8.5 g of methyl iodide are added. The mixture is stirred for a further 3 hours, a further 4.2 g of methyl iodide are added, the cooling source is removed and the mixture is stirred for a further 15 hours. The bulk of the tert.butanol is then removed by evaporation, the residue is taken up in ether, washed neutral with water, dried over sodium sulphate, evaporated and distilled. There are obtained 6 g of 1,1,4-trimethyl-4-propionyl-tetralin of boiling point 79° C./0.05 mmHg; nD20 =1.5249; yield 52%. Odour: fruity, woody.

Workup

  1. stirringThe mixture is stirred for a further 3 hours
  2. customthe cooling source is removed
  3. stirringthe mixture is stirred for a further 15 hours
  4. customThe bulk of the tert.butanol is then removed by evaporation
  5. washwashed neutral with water
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. distillationdistilled

Sources & evidence

ORD record
ord-8785e4103c9b406ca4e69605486ed1bc
Source dataset
uspto-grants-1983_09
Patent number
US04406828

Reaction notes

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