1-Chloro-4-(chloromethyl)benzene → HCID 21249424, compound

HRID 1532788Notes

Reaction equation

HRID 1532788 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Cl)=[CH:4][CH:3]=1.[CH3:10][N:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[CH3:12]>C1(C)C=CC=CC=1>[Cl-:1].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N+:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:11]([CH3:12])[CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 218852-Dimethylaminopyridine

Product 1

HCID 21249424HCID 21249424, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.1313 g (0.00706 mol) p-chlorobenzylchloride, 0.8623 g (0.00706 mol) dimethylaminopyridine, and approximately 10 mL toluene were added to a clean, dry 50 mL round bottom flask equipped with a stir bar, condensor, and drying tube. The reaction apparatus was then lowered into an oil bath at 110° C. The solution became miscible immediately and after 5 minutes a thick white precipitate formed. The reaction was allowed to continue overnight, and after 12 hours was cooled to room temperature. The solvent was removed via rotary evaporation. The resulting solid was recrystallized from ethanol/diethylether to give 1.790 g (89.5%). Calculated for C14H16N2Cl2: C, 59.3765%; H, 5.6944%; N, 9.8917%. Found: C, 57.63%; H, 5.88%; N, 9.59%. 1H NMR (D2O 300 MHZ): δ 3.02 (s 6H), δ 5.15 (s 2H), δ 6.71 (d 2H), δ 7.18 (d 2H), δ 7.30 (d 2H), δ 7.90 (d 2H). Melting point 208-210° C.

Workup

  1. additionwere added to a clean,
  2. customdry 50 mL round bottom flask
  3. customequipped with a stir bar
  4. customcondensor, and drying tube
  5. customThe reaction apparatus was then lowered into an oil bath at 110° C
  6. customa thick white precipitate formed
  7. waitto continue overnight
  8. customThe solvent was removed via rotary evaporation
  9. customThe resulting solid was recrystallized from ethanol/diethylether
  10. customto give 1.790 g (89.5%)

Sources & evidence

ORD record
ord-0a5d248811b34e258ffb162d85d69377
Source dataset
uspto-grants-2001_03
Patent number
US06204386B1

Reaction notes

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