1,2-Dichlorobenzene → HCID 21924059, compound

HRID 485956Notes

Reaction equation

HRID 485956 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8].[NH4+].[Cl-].[CH2:11]1[CH2:15]O[CH2:13][CH2:12]1>CCOCC>[Cl:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH2:13][CH2:12][CH2:11][CH2:15][CH2:15][CH2:11][CH2:12][CH2:13][CH2:7][CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 8028TetrahydrofuranHCID 25517Ammonium Chloride

Product 1

HCID 21924059HCID 21924059, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 0.05 g (0.065 mmoles) of [NitriphosCl]PF6 and 2.00 g (13.61 mmoles) of o-dichlorobenzene in 20 mL of ether at 0° C. was added 19.65 g (13.70 mmoles) of 0.697 mmoles/g of n-dodecylMgBr in THF. The mixture was refluxed overnight, poured into NH4Cl solution, extracted with ether, dried over MgSO4, and the solvent was removed by rotary evaporation. The residue was distilled (101° to 105° C./0.14 mm) to give 1.806 g (6.44 mmoles, 47.4%) of 1-chloro-2-dodecylbenzene. 1H NMR (200 MHz, CDCl3): δ7.4-7.0 (m, 4H), 2.70 (t, J=8 Hz, 2H), 1.6 (m, 2H), 1.3 (br s, 18H), 0.9 (m, 3H). High resolution mass spectrum: calculated for C18H29Cl: 280.1957; Found: 280.1954. Elemental analysis: Calculated for C18H29Cl: C, 76.97; H, 10.41; Found: C, 77.11; H, 10.47. IR(neat): 2935s, 2860s, 1478m, 1470m, 1460sh, 1445m cm-1.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionextracted with ether
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed by rotary evaporation
  5. distillationThe residue was distilled (101° to 105° C./0.14 mm)

Sources & evidence

ORD record
ord-4b432802448848d8affd19c651508239
Source dataset
uspto-grants-1985_08
Patent number
US04538003

Reaction notes

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