Acetic Acid → 1-(2-Propynyl)cyclohexan-1-ol

HRID 259979Notes

Reaction equation

HRID 259979 reaction equation
Cl[C:2](=[CH2:11])[CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[OH-].[K+].C(O)(=O)C>CN(C)C=O>[CH2:3]([C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 11745138HCID 11745138, compound

Product 1

HCID 879381-(2-Propynyl)cyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.00 Grams of the 1-(2'-chloroallyl)-1-cyclohexanol obtained above were dissolved in 94 g of N,N-dimethylformamide, and 9.65 g of potassium hydroxide in a flake form were added. The mixture was stirred at room temperature for 6 hours, and neutralized with a 20% acetic acid aqueous solution. The resultant mixture was subjected to extraction with toluene. The toluene phase was washed with water and dried over magnesium sulfate. The desiccant was filtered off and the toluene was distilled off under reduced pressure to give 7.68 g of 1-propargyl-1-cyclohexanol; m.p.=53°-54° C., FI-MS m/e 138(M+) (Propargyl compound/allene compound=100.0/0.0),

Workup

  1. extractionThe resultant mixture was subjected to extraction with toluene
  2. washThe toluene phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe desiccant was filtered off
  5. distillationthe toluene was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f374e7e5cef14f7889a6e8368c8174ec
Source dataset
uspto-grants-1996_06
Patent number
US05523495

Reaction notes

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