Citric Acid → HCID 23051068, compound

HRID 1651033Notes

Reaction equation

HRID 1651033 reaction equation
[Mg].[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.Cl[Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][Cl:17].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)C.O>[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Si:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][CH2:15][CH2:16][Cl:17])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 2757430Chloro(4-chlorobutyl)dimethylsilaneHCID 5462224Magnesium

Product 1

HCID 23051068HCID 23051068, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

In a 500 ml glass reactor fitted with a mechanically driven stirrer, thermometer, nitrogen inlet, dropping funnel and water-cooled reflux condenser was charged 7.9 g magnesium chip. Via the dropping funnel was added a solution of 47.5 g 4-chlorobenzyl chloride in 200 ml diethyl ether with stirring over a period of 1/2 an hour. After the addition was complete, the reaction was refluxed for 1/2 hour, then cooled to room temperature. To the Grignard reagent was added a solution of 31.0 g chlorodimethyl-4-chloro-n-butylsilane (Petrarch Systems Inc., Bristol, PA) in 50 ml ether. The reaction mixture was refluxed for 1 hour after the addition was complete, then cooled to room temperature. A solution of 10 g citric acid in 200 ml water was added to hydrolyze the reaction. The organic layer was separated, dried over magnesium sulfate and the solvent removed at room temperature under vacuum. Low boiling impurities were removed by distillation at 150° C. under 15 mm vacuum. The residue was a yellow oil. Vapor phase chromatography showed the compound to be about 95 percent pure. Its NMR spectrum was consistent with the expected compound.

Workup

  1. customIn a 500 ml glass reactor fitted with a mechanically driven stirrer
  2. customthermometer, nitrogen inlet, dropping
  3. temperaturereflux condenser
  4. additionAfter the addition
  5. temperaturethe reaction was refluxed for 1/2 hour
  6. temperatureThe reaction mixture was refluxed for 1 hour
  7. additionafter the addition
  8. temperaturecooled to room temperature
  9. customthe reaction
  10. customThe organic layer was separated
  11. dry with materialdried over magnesium sulfate
  12. customthe solvent removed at room temperature under vacuum
  13. customwere removed by distillation at 150° C. under 15 mm vacuum

Sources & evidence

ORD record
ord-1a7d9d918afb4e08995ce783d4a6d86f
Source dataset
uspto-grants-1990_05
Patent number
US04927812

Reaction notes

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