Azobisisobutyronitrile → Cyclohexyl-2-acetoxyethyl-2-carbomethoxy ethylphosphine

HRID 918222Notes

Reaction equation

HRID 918222 reaction equation
[CH:1]1([PH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([O:11][CH:12]=[CH2:13])(=[O:10])[CH3:9].N(C(C)(C)C#N)=NC(C)(C)C#N.[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28]>C1C=CC=CC=1>[CH:1]1([P:7]([CH2:13][CH2:12][O:11][C:8](=[O:10])[CH3:9])[CH2:28][CH2:27][C:26]([O:30][CH3:31])=[O:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6547Azobisisobutyronitrile2×HCID 7294Methyl AcrylateHCID 7904Vinyl AcetateHCID 13199Cyclohexylphosphine

Product 1

HCID 21521357Cyclohexyl-2-acetoxyethyl-2-carbomethoxy ethylphosphine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 23 g. (0.2 mol) of cyclohexylphoshine, 17 g. (0.2 mol) of vinyl acetate and 0.1 g. of azobis-isobutyronitrile in 100 ml. of benzene is prepared and irradiated with ultraviolet light as in Example 1. The temperature is maintained at 25°-30°C. The course of the reaction is followed by observation of the disappearance of the infrared absorption for the vinyl group at 1650 cm.-1After three hours this absorption has disappeared completely and the P-H absorption has shifted from 2450 to 2425 cm.-1 indicating conversion of the primary ##EQU7## absorption to the secondary >P--H. Thus: ##EQU8## To this secondary phosphine intermediate product there is added 18 g. (0.21 mol) of methyl acrylate plus an additional 0.1 g. of azo-bis-isobutyronitrile and irradiation continued under the above conditions for another two hours at which point a scan of the infrared absorption spectrum of the reaction mixture shows the disappearance of the P-H absorption. Removal of the benzene by distillation leaves behind the cyclohexyl-2-acetoxyethyl-2-carbomethoxy ethylphosphine as a colorless, viscous oil.

Workup

  1. customirradiated with ultraviolet light as in Example 1
  2. temperatureThe temperature is maintained at 25°-30°C
  3. customThe course of the reaction is followed by observation of the disappearance of the infrared absorption for the vinyl group at 1650 cm
  4. custom-1After three hours this absorption
  5. customthe P-H absorption
  6. custom-1 indicating conversion of the primary ##EQU7## absorption to the secondary >P--H
  7. additionThus: ##EQU8## To this secondary phosphine intermediate product there is added 18 g
  8. customa scan of the infrared absorption spectrum of the reaction mixture
  9. customthe disappearance of the P-H absorption
  10. customRemoval of the benzene
  11. distillationby distillation

Sources & evidence

ORD record
ord-5a45c9261843491195665799781ce9e4
Source dataset
uspto-grants-1976_07
Patent number
US03970532

Reaction notes

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