Chlorobenzene → Heptylbenzene

HRID 13876

Reaction equation

HRID 13876 reaction equation
O1CCCC1.[CH2:6]([Mg]Cl)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1.CN1CCCC1=O>[C:16]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 7964ChlorobenzeneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 178443917HCID 178443917, compound

Product 1

HCID 14115Heptylbenzene

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A 50-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 1.090 g (8 mmol) of zinc chloride and 4 ml of N-methylpyrrolidinone were weighed in the flask. The flask was purged with argon, followed by stirring. 3.5 ml (7 mmol) of 2M tetrahydrofuran solution of n-heptylmagnesium chloride was added dropwise at 25° C. over a period of 30 minutes, followed by stirring at 25° C. for 30 minutes. The reaction liquid previously obtained was added, followed by stirring at 25° C. for 30 minutes. Further, 0.558 g (5 mmol) of chlorobenzene was added, followed by stirring at 120° C. for 16 hours. After the completion of the reaction, 10 ml of toluene and 10 ml of saturated aqueous ammonium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.684 g of 1-phenylheptane (yield: 78 mol % based on chlorobenzene). The identification of the product was made by mass spectroscopy.

Workup

  1. customA 50-ml four-necked flask was equipped with a stirrer
  2. customThe flask was purged with argon
  3. stirringby stirring at 25° C. for 30 minutes
  4. customThe reaction liquid
  5. custompreviously obtained
  6. additionwas added
  7. stirringby stirring at 25° C. for 30 minutes
  8. stirringby stirring at 120° C. for 16 hours
  9. additionwere added
  10. customfollowed by separation
  11. customThe organic phase was purified by column chromatography

Sources & evidence

ORD record
ord-d6d8dc9dc579454b9f6e82263ada90ec
Source dataset
uspto-grants-2010_06
Patent number
US07728176B2

Linked notes

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