Isopropyl iodide → HCID 54120346, compound

HRID 1576990Notes

Reaction equation

HRID 1576990 reaction equation
[CH3:1][C:2]([CH:7]=[CH:8][CH2:9][CH:10]([CH3:21])[CH2:11][CH2:12][CH2:13][C:14]([CH3:20])([O:16][CH2:17][C:18]#[CH:19])[CH3:15])=[CH:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:28](I)([CH3:30])[CH3:29]>C(C(C)=O)C>[CH:28]([O:5][C:4](=[O:6])[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:8][CH2:9][CH:10]([CH3:21])[CH2:11][CH2:12][CH2:13][C:14]([CH3:20])([O:16][CH2:17][C:18]#[CH:19])[CH3:15])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 54291558HCID 54291558, compound

Product 1

HCID 54120346HCID 54120346, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2.63 g. of 3,7,11-trimethyl-11-(2-propynyloxy)-2,4-dodecadienoic acid are dissolved in 40 ml. of methyl ethyl ketone and then treated with 2.45 g. of potassium carbonate and 6.1 g. of isopropyl iodide. The mixture is heated at reflux under a nitrogen atmosphere for 6 hours, then poured on to ice-water and extracted with ether. The extracts are washed with water and saturated sodium chloride solution, dried and evaporated. By chromatography on silica gel, there is obtained pure 3,7,11-trimethyl-11-(2-propynyloxy)-2,4-dodecadienoic acid isopropyl ester; boiling point (bulb-tube) = 122°C/0.023 mmHg; nD25 = 1.4940.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux under a nitrogen atmosphere for 6 hours
  3. extractionextracted with ether
  4. washThe extracts are washed with water and saturated sodium chloride solution
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-0086214cd9ab44c18d5f2c7a54e97917
Source dataset
uspto-grants-1976_09
Patent number
US03983247

Reaction notes

Loading…