Sodium Hydroxide → Sodium diallyloxyacetate

HRID 2379242Notes

Reaction equation

HRID 2379242 reaction equation
[CH2:1]([O:4][CH:5]([O:12][CH2:13][CH:14]=[CH2:15])[C:6]([O:8]CC=C)=[O:7])[CH:2]=[CH2:3].[OH-].[Na+:17]>C1(C)C=CC=CC=1.O>[CH2:13]([O:12][CH:5]([O:4][CH2:1][CH:2]=[CH2:3])[C:6]([O-:8])=[O:7])[CH:14]=[CH2:15].[Na+:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18958141Prop-2-en-1-yl bis[(prop-2-en-1-yl)oxy]acetate

Product 1

HCID 5173263Sodium diallyloxyacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

21.2 g (0.1 mole) of allyl diallyloxyacetate is dissolved in 42 g of toluene then 3.92 g (98 mmoles) of sodium hydroxide dissolved in 50 g of water is introduced into this solution. This bipbase reaction medium is agitated vigorously for 30 minutes at 30° C., then decanted and the aqueous phase is collected and subjected to a vacuum distillation to eliminate the freed allyl alcohol by azeotropic distillation. The aqueous phase is then poured into acetone to precipitate the expected sodium diallyloxyacetate.

Workup

  1. additionis introduced into this solution
  2. customThis bipbase reaction medium
  3. customdecanted
  4. customthe aqueous phase is collected
  5. distillationsubjected to a vacuum distillation
  6. distillationby azeotropic distillation
  7. additionThe aqueous phase is then poured into acetone
  8. customto precipitate the expected sodium diallyloxyacetate

Sources & evidence

ORD record
ord-6f9ae786a9ec4e03b2b3cebb29066029
Source dataset
uspto-grants-1994_11
Patent number
US05360881

Reaction notes

Loading…