Methyl iodide → HCID 20491273, compound

HRID 435208Notes

Reaction equation

HRID 435208 reaction equation
[Mg].[CH3:2]I.[CH3:4][CH:5]1[CH2:10][CH:9]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:8][CH:7]([CH3:16])[C:6]1=[O:17]>CCOCC>[CH3:2][C:6]1([OH:17])[CH:7]([CH3:16])[CH2:8][CH:9]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:10][CH:5]1[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 20491278Cyclohexanone, 2,6-dimethyl-4-(3-methylbutyl)-

Product 1

HCID 20491273HCID 20491273, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a Grignard solution prepared from magnesium (14.5 g, 0.6 g-atom) and methyl iodide (85.2 g. 0.6 mol) in anhydrous ether (500 mL) was added 2,6-dimethyl-4-(3-methylbutyl) cyclohexanone (59 g, 0.3 mol, produced according to Example 8) over 1 h at 15°-20° C. The mixture was stirred for an additional 1 h and then quenched into saturated ammonium chloride solution. The layers were separated and the aqueous solution was extracted with ether. The combined extracts were washed with 5% sodium bicarbonate solution, brine and then dried. Solvent removal and distillation gave 40 g of the alcohol, bp 92° C. (1 mm). NMR (CDCl3) δ0.8-1.1 (12H, m), 1.1-2.2 (16H, complex pattern with a singlet at 1.2). IR (film) 3550, 1025, 920, 890 cm-1. MS (m/e 212 (M+), 85, 43, 57, 86.

Workup

  1. customquenched into saturated ammonium chloride solution
  2. customThe layers were separated
  3. extractionthe aqueous solution was extracted with ether
  4. washThe combined extracts were washed with 5% sodium bicarbonate solution, brine
  5. customdried
  6. customSolvent removal and distillation

Sources & evidence

ORD record
ord-83757e85757a4bfc9ec2c5a790c54c43
Source dataset
uspto-grants-1983_08
Patent number
US04400545

Reaction notes

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