Ammonia → 1-Ethynyl-cyclohexanecarboxylic acid

HRID 894359Notes

Reaction equation

HRID 894359 reaction equation
[NH2-].[Na+].N.[Na].Cl[C:6]([C:8]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[CH2:7].Cl>CS(C)=O>[C:6]([C:8]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)#[CH:7]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 24533Sodium amideHCID 5360545SodiumHCID 205754641-(1-Chloroethenyl)cyclohexanecarboxylic acid

Product 1

HCID 205754631-Ethynyl-cyclohexanecarboxylic acidYield 66%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of sodium amide in liquid ammonia was prepared using 3.5 g of sodium. After evaporating off the ammonia, the sodium amide was dissolved in 40 cm3 of anhydrous dimethylsulphoxide (DMSO). The mixture was stirred under nitrogen for 3 hours and a solution of 6.6 g (0.035 mole) of 1-(1-chlorovinyl)-1-cyclohexyl-carboxylic acid in 30 cm3 of dry DMSO was added slowly. The temperature of the whole was raised to 50° C. in the course of 6 hours and stirring was continued overnight at laboratory temperature. The mixture was poured into a cold solution of 20% hydrochloric acid. The resulting mixture was extracted several times with ether. After evaporating off the solvent, 1-ethynyl-1-cyclohexyl-carboxylic acid was obtained and this crystallized as colourless crystals on the addition of pentane.

Workup

  1. customwas prepared
  2. customAfter evaporating off the ammonia
  3. dissolutionthe sodium amide was dissolved in 40 cm3 of anhydrous dimethylsulphoxide (DMSO)
  4. stirringstirring
  5. waitwas continued overnight at laboratory temperature
  6. extractionThe resulting mixture was extracted several times with ether
  7. customAfter evaporating off the solvent

Sources & evidence

ORD record
ord-244e7c8de05541799e3e612e8bf2bc1f
Source dataset
uspto-grants-1981_08
Patent number
US04283420

Reaction notes

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