Hydrochloric Acid → HCID 19027104, compound

HRID 1032971Notes

Reaction equation

HRID 1032971 reaction equation
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH:21](Br)[CH3:22])=[CH:17][CH:16]=1)([O-:14])=[O:13].Cl>CS(C)=O>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH:4]([C:3]([O:10][CH3:11])=[O:9])[C:5]([O:7][CH3:8])=[O:6])[CH3:22])=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 110206791-(1-Bromoethyl)-4-nitrobenzene2×

Product 1

HCID 19027104HCID 19027104, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.18 g of sodium hydride (60% and oily) was suspended in 20 ml of dimethyl sulfoxide, and 3.9 g of dimethyl malonate was added dropwise thereto under ice cooling. After the addition, the temperature of the reaction solution was elevated to room temperature, and 3.4 g of 1-(4-nitrophenyl)ethyl bromide synthesized in the above-mentioned section (1) was added thereto, followed by stirring at room temperature for 20 hours in an atmosphere which was shielded from light. The resulting reaction mixture was poured into 1N hydrochloric acid slowly, and the solution was then extracted twice with 50 ml of ether. Extracts were joined together, washed with water and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The solution was then evaporated to dryness, thereby obtaining 3.9 g of dimethyl 1-(4-nitrophenyl)ethylmalonate in an oily state.

Workup

  1. additionAfter the addition
  2. customwas elevated to room temperature
  3. additionwas added
  4. customThe resulting reaction mixture
  5. extractionthe solution was then extracted twice with 50 ml of ether
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe solution was then evaporated to dryness

Sources & evidence

ORD record
ord-a76fa3308e134e7396266b1aff584147
Source dataset
uspto-grants-1994_05
Patent number
US05308848

Reaction notes

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