Acetone → 3E,5E-Pseudoionone

HRID 2352076Notes

Reaction equation

HRID 2352076 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C:7](=[CH:9][CH:10]=O)[CH3:8])[CH3:3].O.[OH-].[Li+].P(=O)(O)(O)O.[CH3:20][C:21]([CH3:23])=[O:22]>>[CH3:3][C:2]([CH3:1])=[CH:4][CH2:5][CH2:6]/[C:7](/[CH3:8])=[CH:9]/[CH:10]=[CH:20]/[C:21]([CH3:23])=[O:22]

Participants

5

Reactant 4

HCID 180Acetone2×HCID 1004Phosphoric AcidHCID 88433,7-Dimethylocta-2,6-Dienal2×HCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 17570033E,5E-Pseudoionone

Procedure

500 g citral (75%) and 2008 g acetone were heated at reflux (50° - 60° C.) in the presence of 5 g lithium hydroxide monohydrate until 1% citral remained. The crude oil was neutralized with 8% aqueous phosphoric acid, stripped of acetone, and washed with water and aqueous sodium bicarbonate to give ann 85% molar yield of pseudoionone. The product contained 1% of isocitral aldol impurities as compared with 3% isocitral aldols in the prior art sodium hydroxide process.

Workup

  1. washwashed with water and aqueous sodium bicarbonate

Sources & evidence

ORD record
ord-a17eadbef47744fe8c63ea077483a3e0
Source dataset
uspto-grants-1989_10
Patent number
US04874900

Reaction notes

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