Water → HCID 13534001, compound

HRID 1285630Notes

Reaction equation

HRID 1285630 reaction equation
[CH3:1][C:2]1[CH2:7]C[C:5](=O)[CH2:4][CH:3]=1.[CH3:9]I.[OH-].[Na+].O.CC[O:16][CH2:17][CH3:18]>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC>[CH3:7][C:2]1([CH3:1])[CH:3]=[C:4]([CH3:5])[CH2:9][CH2:18][C:17]1=[O:16]

Participants

7

Reactant 5

HCID 962WaterHCID 3283Diethyl Ether2×HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 789134-Methylcyclohex-3-en-1-one

Product 1

HCID 13534001HCID 13534001, compound

Reagents, catalysts & solvents 1

HCID 21218Trioctylmethylammonium chlorideCatalyst

Procedure

To a 500 ml 3-neck, round-bottom flask were charged 37.5 g of 88% purity 4-methyl-3-cyclohexen-1-one, 100 ml of ether, 89.5 g of methyl iodide and 0.3 g of methyltrioctylammonium chloride. This mixture was stirred mechanically at ambient temperature and treated with 30 g of granular sodium hydroxide. After 20 minutes at gentle reflux (no cooling used), heat was applied to maintain the reflux for 2 hours longer. The cooled mixture was diluted with ether and treated with water to dissolve the suspended salts. The ether was separated and the aqueous layer was extracted with ether. The combined ether extracts were washed, dried, concentrated and Claisen-distilled to give 36.5 g of the desired product, b.p. 60° C. (10 mm).

Workup

  1. temperatureAfter 20 minutes at gentle reflux (no cooling
  2. temperatureheat
  3. temperatureto maintain the
  4. temperaturereflux for 2 hours longer
  5. dissolutionto dissolve the suspended salts
  6. customThe ether was separated
  7. extractionthe aqueous layer was extracted with ether
  8. washThe combined ether extracts were washed
  9. customdried
  10. concentrationconcentrated
  11. distillationClaisen-distilled

Sources & evidence

ORD record
ord-6ed055254220406b88c8d96a9c81b8a4
Source dataset
uspto-grants-1986_01
Patent number
US04567283

Reaction notes

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