Methyl iodide → HCID 22765513, compound

HRID 442069Notes

Reaction equation

HRID 442069 reaction equation
[CH3:1]I.[CH3:3][C:4]1([CH3:14])[CH2:11][C:10]2([CH3:12])[CH:7]([CH2:8][CH2:9]2)[C:6](=[O:13])[CH2:5]1.[Cl-].[NH4+]>[Mg].CCOCC>[CH3:1][C:6]1([OH:13])[CH2:5][C:4]([CH3:14])([CH3:3])[CH2:11][C:10]2([CH3:12])[CH:7]1[CH2:8][CH2:9]2

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 25517Ammonium ChlorideHCID 227655154,4,6-Trimethylbicyclo[4.2.0]octan-2-one

Product 1

HCID 22765513HCID 22765513, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 5462224MagnesiumCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

To 0.97 g. (0.04 g. atom) of magnesium in a 250 ml. 3-necked round bottomed flask fitted with dropping funnel, magnetic stirrer, and nitrogen inlet was added 25 ml. of ether. Then 5.0 g. (0.035 mole) of methyl iodide in 100 ml. of ether was added from a dropping funnel at such a rate that reflux was maintained as the Grignard reagent was formed. After all the methyl iodide was added, the solution was stirred and refluxed for an additional 1 hour. Then 4.98 g. (0.03 mole) of 4,4,6-trimethylbicyclo[4.2.0]octane-2-one was added in 75 ml. of ether over 30 minutes. After all of the ketone was added, the solution was stirred for an additional 1 hour and then 50 ml. of saturated aqueous ammonium chloride was added. The layers were separated and the aqueous layer was extracted twice with 50 ml. portions of ether. The combined ether layers were dried over sodium sulfate and concentrated in vacuo to yield a solid which was sublimed. The recovered product was 5.3 g. (0.029 mole, 97% yield) of 2,4,4,6-tetramethylbicyclo[4.2.0]octane-2-ol. m.p. 54° - 55° C. nmr: (deuterochloroform): 0.92δ (S-34); 1.02δ (S-34); 1.13δ (S-34); 1.21δ (S-34); 1.28δ - 2.25δ (complex multiplets10H). IR: 3610 cm-1.

Workup

  1. custom3-necked round bottomed flask fitted
  2. additionwas added 25 ml
  3. temperaturethat reflux
  4. customwas formed
  5. temperaturerefluxed for an additional 1 hour
  6. stirringthe solution was stirred for an additional 1 hour
  7. customThe layers were separated
  8. extractionthe aqueous layer was extracted twice with 50 ml
  9. dry with materialThe combined ether layers were dried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customto yield a solid which

Sources & evidence

ORD record
ord-190cd33df66046a6a1d4c90ea88bad29
Source dataset
uspto-grants-1977_08
Patent number
US04044057

Reaction notes

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