Hydrochloric Acid → Diethyl (4-cyanophenyl)propanedioate

HRID 857925Notes

Reaction equation

HRID 857925 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[C:14]([C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1)#[N:15].Cl>O1CCOCC1>[C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:18][CH:17]=1)#[N:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 12162Benzonitrile, 4-bromo-HCID 24758Sodium hydride

Product 1

HCID 11737076Diethyl (4-cyanophenyl)propanedioate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

Diethyl malonate (0.49 mol) was added at approximately 60° C. over 2 hours to a suspension of sodium hydride (0.51 mol) in 140 ml of 1,4-dioxane. After stirring for a further 10 min, 0.05 mol of CuBr were added. After 15 min, 0.25 mol of 4-cyanobromobenzene in 10 ml of dioxane were added. The reaction mixture was maintained at 100° C. for approximately 14 hours and then, at approximately 15° C., 35 ml of 12N hydrochloric acid were slowly added. The precipitate was filtered off and the filtrate was extracted with diethyl ether. After phase separation, the organic phase was dried and then freed from the solvent. 32 g of the title compound remained.

Workup

  1. waitAfter 15 min
  2. filtrationThe precipitate was filtered off
  3. extractionthe filtrate was extracted with diethyl ether
  4. customAfter phase separation
  5. customthe organic phase was dried

Sources & evidence

ORD record
ord-739e99b8780946e5bb2ac9faf981596c
Source dataset
uspto-grants-2006_12
Patent number
US07148227B2

Reaction notes

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