Water → HCID 54359738, compound

HRID 851324Notes

Reaction equation

HRID 851324 reaction equation
[Na].C(OP([CH:10]([Cl:19])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=O)OCC)C.[CH3:20][C:21]([CH3:25])=[CH:22][CH:23]=O.O>C(O)C.O1CCCC1>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([Cl:19])=[CH:23][CH:22]=[C:21]([CH3:25])[CH3:20])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 610203-Methyl-2-butenalHCID 5360545Sodium2×HCID 12874246HCID 12874246, compound

Product 1

HCID 54359738HCID 54359738, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

4.6 g (0.2 mol) of sodium were dissolved incrementally in 100 ml of dry ethanol. When all the sodium had dissolved, 100 ml of anhydrous tetrahydrofuran were added and 58.4 g (0.2 mol) of 4-methoxy-α-chloro-benzyl-phosphonic acid diethyl ester, dissolved in 50 ml of anhydrous tetrahydrofuran, were added dropwise at 0° C., while stirring. After stirring had been continued at 0°-10° C. for a further 1 hour, 16.8 g (0.2 mol) of β,β-dimethylacrolein, dissolved in 30 ml of anhydrous tetrahydrofuran, were added dropwise, while stirring. Stirring was then continued at room temperature for a further 12 hours. 600 ml of water were then added to the reaction mixture and the mixture was extracted twice with 300 ml of methylene chloride each time. The organic phase was separated off and dried over magnesium sulphate, the solvent was distilled off under a waterpump vacuum and the residue was distilled in vacuo. 25 g of 1-(4'-methoxyphenyl)-1-chloro-4,4-dimethyl-1,3-butadiene (isomer mixture) were obtained as a yellow oil which had a boiling point of 130°-145° C./2 mm Hg and partially crystallized after some time.

Workup

  1. additionwere added dropwise at 0° C.
  2. stirringAfter stirring
  3. additionwere added dropwise
  4. stirringwhile stirring
  5. stirringStirring
  6. waitwas then continued at room temperature for a further 12 hours
  7. extractionthe mixture was extracted twice with 300 ml of methylene chloride each time
  8. customThe organic phase was separated off
  9. dry with materialdried over magnesium sulphate
  10. distillationthe solvent was distilled off under a waterpump vacuum
  11. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-4480576153254bc3a67258c4e8566494
Source dataset
uspto-grants-1983_05
Patent number
US04384114

Reaction notes

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