Dichloromethane → HCID 611809, compound

HRID 543525Notes

Reaction equation

HRID 543525 reaction equation
Cl[CH2:2][Cl:3].Cl[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[OH-].[Na+]>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:3][C:2]1[CH:11]=[CH:12][CH:5]=[CH:6][C:7]=1[CH:8]=[CH:9][C:8]1[CH:11]=[CH:12][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 77264-ChlorobenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 611809HCID 611809, compound

Reagents, catalysts & solvents 2

HCID 70671Benzyltriphenylphosphonium chlorideCatalystHCID 962WaterSolvent

Procedure

A 25 ml reaction flask was charged with 12.42 gram (0.03 moles) of polyvinyl benzyl triphenyl phosphonium chloride, 60 ml of dichloromethane, and 14.0 gm (0.10 moles) of p-chlorobenzaldehyde. A magnetic stirr bar was added and a thermometer and a condenser were attached. 20 grams of 50% aqueous NaOH solution was added all at once to the reaction flask. The temperature of the reaction mixture rose to a reflux and was stirred for one hour. 100 ml of H2O was added and the organic layer was separated. The polymer was precipitated from an excess of methanol. 5.55 grams of a white fibrous polymer was obtained. The polymer was continuously extracted with methanol for 24 hours before being dried and submitted for elemental analysis for % Cl and % P. A calculated percent is 14.7% Cland 0.0% P. The analysis indicated 14.55% Cl and 0.3% P.

Workup

  1. customA 25 ml reaction flask
  2. additionA magnetic stirr bar was added
  3. temperaturea reflux
  4. customthe organic layer was separated
  5. customThe polymer was precipitated from an excess of methanol

Sources & evidence

ORD record
ord-05f9094cfbcb45fa8fde077c48ae282d
Source dataset
uspto-grants-1984_05
Patent number
US04446284

Reaction notes

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