p-Toluenesulfonic acid → HCID 21511395, compound

HRID 1605811Notes

Reaction equation

HRID 1605811 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]1[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:26][C:27](CC)=[O:28]>>[C:1]([CH2:3][CH:4]1[CH2:8][CH2:7][C:6]2([O:28][CH2:27][CH2:26][O:9]2)[CH:5]1[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])#[N:2]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6569Methyl Ethyl KetoneHCID 21511388HCID 21511388, compound

Product 1

HCID 21511395HCID 21511395, compoundYield 73.4%

Procedure

Into a 2 liter flask fitted with a 1 meter adiabatic column provided with a metallic lining, are placed: 400 g of 3-cyanomethyl-2-n-pentyl-1-cyclopentanone, 522 g of the glycoketal of methylethyl ketone and 4.5 g of paratoluenesulphonic acid. The mass is progressively heated in order to slowly distil the methyl ethyl ketone from the head of the column (temperature of the mass 128°-132°C; temperature of the vapour 80°C). The operation lasts about 5 hours. Then the excess glycoketal of methylethyl ketone is removed (temperature of the mass 132°-135°C; temperature of the vapour 110°-112°C). The mass is then cooled, 30 g of dry sodium carbonate added thereto, stirred for a half-hour and the mass washed to neutrality after diluting with 200 ml of ethyl ether. After distillation of the solvent and rectification of the crude product, there is obtained 360 g of 3-cyanomethyl-1,1-ethylenedioxy-2-n-pentyl-cyclopentane, which represents a yield of 73.4%. The product exhibits the following constants: b.p.0.5 = 136°-138°C, nD15 = 1.4724.

Workup

  1. customInto a 2 liter flask fitted with a 1 meter adiabatic column
  2. customprovided with a metallic lining
  3. temperatureThe mass is progressively heated in order
  4. customto slowly distil the methyl ethyl ketone from the head of the column (temperature of the mass 128°-132°C
  5. customtemperature of the vapour 80°C
  6. customThen the excess glycoketal of methylethyl ketone is removed (temperature of the mass 132°-135°C
  7. customtemperature of the vapour 110°-112°C
  8. temperatureThe mass is then cooled
  9. addition30 g of dry sodium carbonate added
  10. washthe mass washed to neutrality
  11. additionafter diluting with 200 ml of ethyl ether
  12. distillationAfter distillation of the solvent and rectification of the crude product

Sources & evidence

ORD record
ord-f46d7999fc474240871f821b13b680b0
Source dataset
uspto-grants-1976_04
Patent number
US03951876

Reaction notes

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