Hydrochloric Acid → 2,2'-methanediyldicyclohexanone

HRID 1105964Notes

Reaction equation

HRID 1105964 reaction equation
CC1[O:7][CH:6]([CH3:8])OC(C)O1.[OH-].[K+].[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl>CO>[CH2:14]([CH:13]1[CH2:12][CH2:17][CH2:16][CH2:8][C:6]1=[O:7])[CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C:12]1=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7967CyclohexanoneHCID 14797Potassium HydroxideHCID 31264Paraldehyde

Product 1

HCID 37551872,2'-methanediyldicyclohexanoneYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture comprising 68 g of paraldehyde, 6 g of caustic potash and 188 g of methanol was added dropwise to a solution comprising 1,000 g of cyclohexanone and 188 g of methanol at 60°-70° C. over a period of 2 hours, and the resulting mixture was stirred for another 3 hours at 60°-70° C. Thereafter, the reaction mixture was decomposed with dilute hydrochloric acid, extracted with ether, washed first with 3% aqueous sodium carbonate, then with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. After recovering the solvent, the dried product was distilled under vacuum to provide 340 g (yield: 64%) of a fraction boiling at 135°-145° C./3 mm Hg.

Workup

  1. additionwas added dropwise to a solution
  2. customat 60°-70° C.
  3. customof 2 hours
  4. extractionextracted with ether
  5. washwashed first with 3% aqueous sodium carbonate
  6. dry with materialwith saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate
  7. customAfter recovering the solvent
  8. distillationthe dried product was distilled under vacuum
  9. customto provide 340 g (yield: 64%) of a fraction boiling at 135°-145° C./3 mm Hg

Sources & evidence

ORD record
ord-73748befc89a462d918191ee1065e858
Source dataset
uspto-grants-1982_01
Patent number
US04310685

Reaction notes

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