Acetic Anhydride → HCID 19995349, compound

HRID 2248981Notes

Reaction equation

HRID 2248981 reaction equation
[C:1]([O:10][CH:11]([CH3:13])[CH3:12])(=[O:9])[CH2:2][C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4].[CH:14]([O:23][CH:24]([CH3:26])[CH3:25])([O:19][CH:20]([CH3:22])[CH3:21])OC(C)C.C(OC(=O)C)(=O)C>>[C:3]([O:5][CH:6]([CH3:8])[CH3:7])(=[O:4])[CH2:2][C:1]([O:10][CH:11]([CH3:12])[CH3:13])=[O:9].[CH:11]([O:10][CH:1]=[C:2]([C:14]([O:19][CH:20]([CH3:21])[CH3:22])=[O:23])[C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4])([CH3:12])[CH3:13].[CH:24]([O:23][CH:14]([O:19][CH:20]([CH3:21])[CH3:22])[CH:2]([C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4])[C:1]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 78191Propane, 2,2',2''-[methylidynetris(oxy)]tris-HCID 83223Diisopropyl malonate

Product 3

HCID 83223Diisopropyl malonateYield 7.6%HCID 19995349HCID 19995349, compoundYield 80.2%HCID 19995351HCID 19995351, compoundYield 6.5%

Conditions

Temperature
-10 °C

Procedure

188 g (1 mol) of diisopropyl malonate, 571 g (3 mol) of triisopropyl orthoformate and 0.05 g of catalyst from Example 5 were initially introduced into the apparatus mentioned in Example 1 and the mixture was heated to -10° C. 102 g of acetic anhydride were then metered in over the course of 5 hours. The bottom temperature was raised to 150° C. At the same time a low-boiling fraction was removed under reflux at a boiling temperature of 60° C. After 10 hours, the formation of low-boiling component decreased. The mixture was then fractionated in vacuo, first at 15 mbar and then at 0.3 mbar. 7.6% of diisopropyl malonate, 80.2% of diisopropyl isopropoxymethylenemalonate and 6.5% of diisopropyl diisopropoxy-methylmalonate were obtained. The last-mentioned compound was converted into diisopropyl isopropoxymethylenemalonate by heating with 0.2 g of H3PO4.

Workup

  1. customwere then metered in over the course of 5 hours
  2. temperatureThe bottom temperature was raised to 150° C
  3. customAt the same time a low-boiling fraction was removed
  4. temperatureunder reflux at a boiling temperature of 60° C

Sources & evidence

ORD record
ord-1d3da4a9b11345e4b91dff7a76115b89
Source dataset
uspto-grants-1991_08
Patent number
US05041619

Reaction notes

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