p-Toluenesulfonic acid → HCID 68141672, compound

HRID 1576546Notes

Reaction equation

HRID 1576546 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH:5]1[CH2:10]/[CH:11]=[CH: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]/[CH:11]=[CH:12]\[CH2:13][CH3:14])#[N:2]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6569Methyl Ethyl KetoneHCID 70626846HCID 70626846, compound

Product 1

HCID 68141672HCID 68141672, compound

Procedure

Into a 2 liter flask fitted with a 1 meter adiabatic column provided with a metallic lining, are placed: 212 g of 3-cyanomethyl-2-(cis-2-n-pentenyl)-1-cyclopentanone, 512 g of the glycoketal of methylethyl ketone and 2.1 g of para-toluenesulphonic 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 120°-140°C; temperature of the vapour 77°-79°C). The operation lasts about 9 hours. The mass is then cooled, 10 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 229.2 g of 3-cyanomethyl-1,1-ethylenedioxy-2-(cis-2-n-pentenyl)-cyclopentane. The product exhibits the following constants: b.p.0.5 = 130°C, nD15 = 1.4862. The infra-red spectrum had principal bands at: 2240, 1650, 730, 1150, 1115 and 1040 cm-1. NMR Spectrum: 0.95, 4.82, 5.36.

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 120°-140°C
  5. customtemperature of the vapour 77°-79°C
  6. temperatureThe mass is then cooled
  7. addition10 g of dry sodium carbonate added
  8. washthe mass washed to neutrality
  9. additionafter diluting with 200 ml of ethyl ether
  10. distillationAfter distillation of the solvent and rectification of the crude product

Sources & evidence

ORD record
ord-2e2718fcf8ae47cba26458e7b9c74527
Source dataset
uspto-grants-1976_09
Patent number
US03981891

Reaction notes

Loading…