Dimethyl Sulfoxide → HCID 54424551, compound

HRID 259000Notes

Reaction equation

HRID 259000 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[C:5]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:27][CH:26]=1)([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:14][CH:13]=1)C(OCC)=O)[CH3:2].[Cl-].[Na+].CS(C)=O>O>[CH2:1]([O:3][C:4](=[O:37])[CH:5]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:16][CH:17]=1)[CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:29][CH:30]=1)[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 635081Propanedioic acid, bis[[4-(2,2-dimethyl-1-oxopropyl)phenyl]methyl]-, diethyl ester

Product 1

HCID 54424551HCID 54424551, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 50.0 g. (0.100 mole) bis(p-pivaloylbenzyl)malonic acid diethylester, 6.0 g. (0.103 mole) sodium chloride, 200 ml. dimethylsulfoxide and 3.5 ml. water is heated at 180° for 22 hours. The resulting mixture is then cooled and poured into water. The water mixture is extracted twice with methylene chloride and the methylene chloride washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The resulting oil is crystallized from pentane to give bis(p-pivaloylbenzyl) acetic acid ethyl ester; m.p. 60°-63° C.

Workup

  1. additionA mixture of 50.0 g
  2. temperatureThe resulting mixture is then cooled
  3. extractionThe water mixture is extracted twice with methylene chloride
  4. washthe methylene chloride washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting oil is crystallized from pentane

Sources & evidence

ORD record
ord-5ebb00fd49b64abf88e9c9980bf54606
Source dataset
uspto-grants-1977_07
Patent number
US04035508

Reaction notes

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