Ethanol → HCID 21331125, compound

HRID 1729666Notes

Reaction equation

HRID 1729666 reaction equation
[Na].C([C:4](CC)([C:8]([O-:10])=[O:9])[C:5]([O-:7])=[O:6])C.[CH3:13][CH2:14]OCC.[CH2:18]([O:20][C:21](=[O:26])[C:22](Br)([CH3:24])[CH3:23])[CH3:19].[CH2:27](O)[CH3:28]>O.C(O)(=O)C>[C:21]([C:22]([CH:4]([C:8]([O:10][CH2:27][CH3:28])=[O:9])[C:5]([O:7][CH2:13][CH3:14])=[O:6])([CH3:24])[CH3:23])([O:20][CH2:18][CH3:19])=[O:26]

Participants

8

Reactant 5

HCID 702EthanolHCID 3283Diethyl EtherHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 5360545SodiumHCID 69515632,2-Diethylpropanedioate

Product 1

HCID 21331125HCID 21331125, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 13.8 g. (0.6 mol.) of sodium in absolute ethanol is added a solution of 96 g. (0.6 mol.) of diethylmalonate in 500 ml. of ether. The mixture is cooled and 117.1 g. (0.6 mol.) of 2-bromo-2-methylpropionic acid ethyl ester is added. The reaction mixture is warmed for 2 hours, then stirred at ambient temperature for 48 hours. Acetic acid and water are added, the layers are separated and the ethereal phase is washed with water, dried (MgSO4) and evaporated to dryness to give diethyl 2-(1-carbethoxy-1-methylethyl)malonate.

Workup

  1. temperatureThe mixture is cooled
  2. temperatureThe reaction mixture is warmed for 2 hours
  3. customthe layers are separated
  4. washthe ethereal phase is washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-b48c1424a314489fbc42e0a4d7680f53
Source dataset
uspto-grants-1976_11
Patent number
US03989694

Reaction notes

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