Allyl Alcohol → HCID 178460557, compound

HRID 1763225Notes

Reaction equation

HRID 1763225 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:11])[CH:9]=[CH2:10].[CH3:12][CH:13]=[CH:14][PH:15](Cl)=[O:16]>C(Cl)(Cl)Cl>[CH2:8]([O:11][PH:15]([CH2:14][CH:13]=[CH2:12])=[O:16])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 178460679HCID 178460679, compound

Product 1

HCID 178460557HCID 178460557, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

202 g of triethyl amine (2 mols) were added while stirring at 0° to 5° C. to a solution of 116 g of allyl alcohol (2 mols) in 1 l of anhydrous chloroform and then 249 g of methylvinyl phosphinic acid chloride (2 mols) were added dropwise over a period of about 1 hour. After suction filtration, the solid residue (triethyl amine hydrochloride) was dissolved in water, the emerging oily layer was separated and combined with the filtrate. To remove the chloride ions the filtrate was shaken 4 times, each time with 600 ml of water, dried over sodium sulfate and the chloroform was distilled off in a rotary evaporator. The brown oily residue was distilled under a pressure of 0.01 mm at a temperature of the oil bath of 40° C. 85 g of a colorless liquid were obtained.

Workup

  1. filtrationAfter suction filtration
  2. dissolutionthe solid residue (triethyl amine hydrochloride) was dissolved in water
  3. customthe emerging oily layer was separated
  4. customTo remove the chloride ions the filtrate
  5. dry with materialeach time with 600 ml of water, dried over sodium sulfate
  6. distillationthe chloroform was distilled off in a rotary evaporator
  7. distillationThe brown oily residue was distilled under a pressure of 0.01 mm at a temperature of the oil bath of 40° C

Sources & evidence

ORD record
ord-be4a1c7474ae44d68787c28cbbf87cf7
Source dataset
uspto-grants-1978_09
Patent number
US04111900

Reaction notes

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