Carbon Tetrachloride → HCID 22106943, compound

HRID 1456605Notes

Reaction equation

HRID 1456605 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[C:4]([O:10][CH2:11][O:12][CH3:13])[CH:3]=1.C(Cl)(Cl)(Cl)[Cl:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][Cl:15])=[C:4]([O:10][CH2:11][O:12][CH3:13])[CH:3]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 10560064HCID 10560064, compound

Product 1

HCID 22106943HCID 22106943, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.69 g of 4-chloro-2-methoxymethoxybenzyl alcohol [prepared as described in step (b) above] were dissolved in 80 ml of tetrahydrofuran, and then 7.11 g of carbon tetrachloride and 12.14 g of triphenylphosphine were added to the resulting solution. The resulting mixture was stirred at room temperature for 1 hour and then heated under reflux for 2.5 hours. At the end of this time, any insoluble substance was removed by filtration, and the filtrate was concentrated by evaporation under reduced pressure. The residue was purified by silica gel column chromatography, using a 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.38 g (yield 66%) of the title compound as an oily substance.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours
  3. customAt the end of this time, any insoluble substance was removed by filtration
  4. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-8c9b94bc57e94ea79dcadbf1c6b5dab1
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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