HCID 68141204, compound → HCID 68140436, compound

HRID 1576548Notes

Reaction equation

HRID 1576548 reaction equation
[CH2:1]([CH:6]1[CH:10]([CH:11](C(OCC)=O)[C:12](=[O:14])[CH3:13])[CH2:9][CH2:8][C:7]1=[O:20])/[CH:2]=[CH:3]\[CH2:4][CH3:5]>O>[CH2:1]([CH:6]1[CH:10]([CH2:11][C:12](=[O:14])[CH3:13])[CH2:9][CH2:8][C:7]1=[O:20])/[CH:2]=[CH:3]\[CH2:4][CH3:5]

Participants

3

Reactant 1

HCID 68141204HCID 68141204, compound

Product 1

HCID 68140436HCID 68140436, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Into a 1 liter autoclave, there are introduced: 54.7 g of 2-(cis-2-n-pentenyl)-3-(1-carbethoxy-2-oxopropyl)-1-cyclopentanone and 110 g of distilled water. The autoclave is evacuated and then rapidly heated to 150°C, which temperature is maintained for 3 hours. After cooling and decompression, the mass is extracted with benzene. The benzene solutions are washed with water distilled and rectified to yield 16.2 g of 2-(cis-2-n-pentenyl)-3-(2-oxopropyl)-1-cyclopentanone. Physical constants: b.p.0.5 = 112°-113°C; nD15 = 1.4785. IR Spectrum: 1740, 1715, 1405, 1355, 1155, 970 and 1670 cm-1. NMR Spectrum: 0.94, 2.08 and 5.34. The compound can be represented by the formula ##SPC26##

Workup

  1. additionInto a 1 liter autoclave, there are introduced
  2. customThe autoclave is evacuated
  3. temperaturewhich temperature is maintained for 3 hours
  4. temperatureAfter cooling
  5. extractiondecompression, the mass is extracted with benzene
  6. washThe benzene solutions are washed with water
  7. distillationdistilled

Sources & evidence

ORD record
ord-70c9549bea17498d8a5e904561b4a8ee
Source dataset
uspto-grants-1976_09
Patent number
US03981891

Reaction notes

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