Diethyl Ether → Silver alpha-methylacetoacetate

HRID 2245817Notes

Reaction equation

HRID 2245817 reaction equation
N(CCO)CCO.CCOCC.[CH2:13]([CH:15]([C:19]([CH3:21])=[O:20])[C:16]([OH:18])=[O:17])C.[N+]([O-])([O-])=O.[Ag+:26]>O>[CH3:13][CH:15]([C:19]([CH3:21])=[O:20])[C:16]([O-:18])=[O:17].[Ag+:26]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8113DiethanolamineHCID 204932-Ethyl-3-oxobutanoic acidHCID 24470Silver Nitrate

Product 1

HCID 86633513Silver alpha-methylacetoacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Diethanolamine (4.4 g) was dissolved in water (5 mL), and this solution was added to the ether solution of α-ethylacetoacetic acid while cooling with ice. Next, a solution of silver nitrate (6.8 g) dissolved in water (8 mL) was added dropwise. The white precipitate that precipitated was filtered off, washed with ice water and then isopropanol, and dried, yielding silver α-methylacetoacetate as a white precipitate (yield 6.7 g). FIG. 6 shows the infrared absorption spectrum (IR) of the silver α-methylacetoacetate that was obtained. IR:1700 cm−1, 1547 cm−1.

Workup

  1. temperaturewhile cooling with ice
  2. additionwas added dropwise
  3. customThe white precipitate that precipitated
  4. filtrationwas filtered off
  5. washwashed with ice water
  6. dry with materialisopropanol, and dried

Sources & evidence

ORD record
ord-be84490065db484b8c8bf7ca19fdaf63
Source dataset
uspto-grants-2010_03
Patent number
US07683195B2

Reaction notes

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