Carbon Tetrachloride → Ethyl 2-[4-(2,2-dichlorovinyl)phenyl]propionate

HRID 637610Notes

Reaction equation

HRID 637610 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC.C(OCC)(=O)C.[C:47](Cl)(Cl)([Cl:49])[Cl:48]>>[Cl:48][C:47]([Cl:49])=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1

Participants

6

Reactant 5

HCID 5943Carbon TetrachlorideHCID 8058Hexane2×HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 13066570rac 2-(4-Formylphenyl)propionic Acid Ethyl Ester

Product 1

HCID 13388016Ethyl 2-[4-(2,2-dichlorovinyl)phenyl]propionate

Conditions

Temperature
50 °C

Procedure

In 260 ml of carbon tetrachloride were dissolved 60 g of ethyl 2-(4-formylphenyl)propionate and 122 g of triphenylphosphine, followed by stirring in a stream of nitrogen gas at 50° C. for 4.5 hours. After cooling, the mixture was poured into 1 l of cold n-hexane and filtered. The filtrate was concentrated under reduced pressure to give an oily substance, which was subjected to silica gel column chromatography (eluent: n-hexane--ethyl acetate=40:1) to obtain 29 g of ethyl 2-[4-(2,2-dichlorovinyl)phenyl]propionate (ST-5) as an oily substance, b.p.0.2-0.3 128°-129° C.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give an oily substance, which

Sources & evidence

ORD record
ord-aba7aa42ef834a13bc5e27081e0e5eb7
Source dataset
uspto-grants-1985_12
Patent number
US04557871

Reaction notes

Loading…