Water → I2-Ionone

HRID 1285233Notes

Reaction equation

HRID 1285233 reaction equation
[CH3:1][C:2]([CH3:14])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:13])=[CH:7]/[CH:8]=[CH:9]/[C:10]([CH3:12])=[O:11].S(=O)(=O)(O)O.O>C(Cl)Cl>[CH3:13][C:6]1[CH2:5][CH2:4][CH2:3][C:2]([CH3:14])([CH3:1])[C:7]=1/[CH:8]=[CH:9]/[C:10]([CH3:12])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 17570033E,5E-Pseudoionone

Product 1

HCID 638014I2-IononeYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 600 g of a 96% pure pseudoionone in 1,200 ml of methylene chloride was introduced continuously in the course of 10 minutes, while stirring vigorously (800 rpm), through one of the two connections of the reactor, and 1,000 ml of a 96% strength sulfuric acid were fed in simultaneously through the other connection. The product, which was discharged at 42° C., was hydrolyzed in a downstream thin film reactor with 2,000 ml of water, the organic phase was separated off, washed neutral with 2% strength sodium carbonate solution and then with water and freed from solvent under reduced pressure, and the residue was then distilled under 0.2 mbar. 495 g of 97.0% pure β-ionone were obtained, corresponding to a yield of β-ionone of 83.3% of theory. In this case too, the residue produced was a resin which exhibited good flow.

Workup

  1. customwas discharged at 42° C.
  2. customthe organic phase was separated off
  3. washwashed neutral with 2% strength sodium carbonate solution
  4. distillationthe residue was then distilled under 0.2 mbar

Sources & evidence

ORD record
ord-cdc24693777c4f1db3afc431ab80a8c3
Source dataset
uspto-grants-1986_01
Patent number
US04565894

Reaction notes

Loading…