Heptylbenzene → HCID 18417656, compound

HRID 1534682Notes

Reaction equation

HRID 1534682 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:18][O:19]C(Cl)Cl>[N+](CC)([O-])=O.ClC(Cl)C>[CH2:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[CH:18]=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 14115HeptylbenzeneHCID 21004Methane, dichloromethoxy-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 18417656HCID 18417656, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolvent2×HCID 6587NitroethaneSolvent

Procedure

To a solution of 87.7 g of n-heptylbenzene in a mixture of 160 ml of nitroethane and 480 ml of dichloroethane was added little by little 79.5 g of anhydrous aluminum chloride with ice cooling, followed by adding dropwise a solution of 54.5 ml. of dichloromethyl methyl ether in 60 ml of dichloroethane. After completion of the addition, the reaction was carried out at 0° C. for a further one hour. The reaction mixture was poured into ice water and extracted with chloroform. The organic layer was washed with water and dried, and the solvent was evaporated. The residue was chromatographed on silica gel column with a solvent of n-hexane - isopropyl ether (10:1) to give 17.3 g of 2-heptylbenzaldehyde as a colorless oil from the first eluted fractions and 64.8 g of 4-heptylbenzaldehyde as a colorless oil from the later eluted fractions.

Workup

  1. additionby adding dropwise a solution of 54.5 ml
  2. additionAfter completion of the addition
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customThe residue was chromatographed on silica gel column with a solvent of n-hexane - isopropyl ether (10:1)

Sources & evidence

ORD record
ord-4184093f78c4474ba316de109adcba74
Source dataset
uspto-grants-1992_02
Patent number
US05089654

Reaction notes

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