Diethyl phenylmalonate → Tetra-n-butyl ammonium diethylphenyl malonate

HRID 258376

Reaction equation

HRID 258376 reaction equation
[OH-].[CH2:2]([N+:6]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][CH3:5].[CH2:19]([O:21][C:22](=[O:35])[CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:20]>C1(C)C=CC=CC=1>[CH2:27]([O:26][C:24](=[O:25])[CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:22]([O:21][CH2:19][CH3:20])=[O:35])[CH3:28].[CH2:15]([N+:6]([CH2:2][CH2:3][CH2:4][CH3:5])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 66514Diethyl phenylmalonateHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 86747399Tetra-n-butyl ammonium diethylphenyl malonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a three necked 100 mL round bottom flask fitted with a argon inlet, dropping funnel, distillation unit and magnetic needle, was added 7.7 mmoles of tetrabutylammonium hydroxide (20% solution in toluene/methanol) in 40 mL of dry toluene and heated to +75° C. to +85° C. Diethylphenylmalonate (9.3 mmoles) was slowly added. Simultaneously an azeotrope of toluene-water was distilled out slowly over a period of 3 hours. After all toluene had distilled over, the flask was cooled to room temperature slowly. A solid product separated out, which was repeatedly washed with dry hexane. The initiator (tetra-n-butyl ammonium diethylphenyl malonate) thus formed was dried in vacuum and stored at room temperature under nitrogen or argon.

Workup

  1. customTo a three necked 100 mL round bottom flask fitted with a argon inlet
  2. distillationdistillation unit and magnetic needle
  3. temperatureheated to +75° C. to +85° C
  4. distillationSimultaneously an azeotrope of toluene-water was distilled out slowly over a period of 3 hours
  5. distillationAfter all toluene had distilled over, the flask
  6. customA solid product separated out
  7. washwhich was repeatedly washed with dry hexane

Sources & evidence

ORD record
ord-b91e56431fe24450a0867bd0ab3b335c
Source dataset
uspto-grants-1993_11
Patent number
US05266702

Linked notes

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