Water → Propanedioic acid, bis[[4-(2,2-dimethyl-1-oxopropyl)phenyl]methyl]-, diethyl ester

HRID 1657917Notes

Reaction equation

HRID 1657917 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:18][CH:17]=1.[OH2:28]>CC(N(C)C)=O>[CH2:12]([O:11][C:3](=[O:10])[C:4]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:28])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:18][CH:17]=1)([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:18][CH:17]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 128310071-[4-(Bromomethyl)phenyl]-2,2-dimethylpropan-1-one

Product 1

HCID 635081Propanedioic acid, bis[[4-(2,2-dimethyl-1-oxopropyl)phenyl]methyl]-, diethyl ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Procedure

To a cold suspension of 4.66 g (0.194) mole of sodium hydride in 200 ml dimethylacetamide there is added dropwise 28.2 g (0.176 mole) diethyl malonate in 80 ml of dimethylacetamide maintaining the temperature between 0° and 5°C. Stirring is initiated for two hours at room-temperature and there is then added 40.8 g(0.16 mole) of α-bromo-p-pivaloyl toluene in 200 ml of dimethylacetamide maintaining the reaction temperature between 20° and 30°C. Stirring is continued overnight at room temperature. Water is then added and the excess dimethylacetamide is removed in vacuo, and the resulting residue is partitioned between petroleum ether and water. The layers are washed with water, and salt water, dried and evaporated in vacuo. The residue is then distilled in vacuo and crystallized from petroleum ether at -50°C to give bis-(p-pivaloylbenzyl)malonic acid diethyl ester, m.p. 65° to 67°C.

Workup

  1. stirringStirring
  2. waitis continued overnight at room temperature
  3. customthe excess dimethylacetamide is removed in vacuo
  4. customthe resulting residue is partitioned between petroleum ether and water
  5. washThe layers are washed with water, and salt water
  6. customdried
  7. customevaporated in vacuo
  8. distillationThe residue is then distilled in vacuo
  9. customcrystallized from petroleum ether at -50°C

Sources & evidence

ORD record
ord-a6ac04d24b5b44f991a0ff95daaf788c
Source dataset
uspto-grants-1976_06
Patent number
US03962320

Reaction notes

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