Methanol → 2-Bromo-1-(1-methylcyclohexyl)ethan-1-one

HRID 1679669Notes

Reaction equation

HRID 1679669 reaction equation
[Br:1]Br.C(Cl)(Cl)Cl.[CH3:7][C:8]([C:10]1([CH3:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9].CO>BrBr.O>[CH3:16][C:10]1([C:8]([CH2:7][Br:1])=[O:9])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 24408Bromine2×HCID 5441981-(1-methylcyclohexyl)ethanone

Product 1

HCID 214750112-Bromo-1-(1-methylcyclohexyl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 962WaterSolvent

Procedure

A solution of 328 g. bromine in 300 ml. chloroform was added gradually to a stirred solution of 300 g. 1-methylcyclohexyl methyl ketone in 100 ml. methanol. After the addition of a few drops of bromine solution at 15° C. the reaction mixture was cooled and maintained between 0° - 5° C. The reaction mixture was stirred for 10 minutes, after the addition of bromine had been completed, and then poured on to a mixture of crushed ice and water. The water layer was separated from the organic liquid and extracted with methylene chloride. The extract and the organic portion were combined and washed with water followed by a saturated solution of sodium bicarbonate and then finally with water. After drying over calcium chloride the liquid was evaporated and distilled to give bromomethyl 1-methylcyclohexyl ketone, b.p. 76° - 78° C./0.1 mm. Hg.

Workup

  1. temperaturewas cooled
  2. temperaturemaintained between 0° - 5° C
  3. customThe water layer was separated from the organic liquid
  4. extractionextracted with methylene chloride
  5. extractionThe extract
  6. washwashed with water
  7. dry with materialAfter drying over calcium chloride the liquid
  8. customwas evaporated
  9. distillationdistilled

Sources & evidence

ORD record
ord-3a23297d93a3499aad04d3d9c5ab1bfb
Source dataset
uspto-grants-1978_03
Patent number
US04081540

Reaction notes

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