Carbon Tetrachloride → HCID 22345410, compound

HRID 743380Notes

Reaction equation

HRID 743380 reaction equation
[C:1]([Cl:5])(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:25][O:26][CH2:27][O:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1CO>O1CCCC1>[CH3:25][O:26][CH2:27][O:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:1][Cl:5]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 109209042-Methoxymethoxybenzyl alcohol

Product 1

HCID 22345410HCID 22345410, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

16.4 ml of carbon tetrachloride, followed by 44.5 g of triphenylphosphine were added, whilst ice-cooling, to a solution of 23.8 g of 2-methoxymethoxybenzyl alcohol in 240 ml of tetrahydrofuran, and the resulting mixture was heated under reflux for 5 hours. At the end of this time, the mixture was cooled, insoluble materials were filtered off and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 9:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 15.5 g (yield 57%) of the title compound as a colorless liquid.

Workup

  1. additionwere added, whilst ice-
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 5 hours
  4. temperatureAt the end of this time, the mixture was cooled
  5. filtrationinsoluble materials were filtered off
  6. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through silica gel
  8. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-9d3c7f253c8240e88b25e7d97ab51fb8
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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