Cycloheptylbenzene → 4-Cycloheptyl-benzaldehyde

HRID 1415326Notes

Reaction equation

HRID 1415326 reaction equation
[CH:1]1([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2C=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C2C=CC=CC=2)CCCCCC1.Cl[CH:30]([O:32]C(Cl)Cl)Cl>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH:1]1([C:8]2[CH:9]=[CH:12][C:13]([CH:30]=[O:32])=[CH:14][CH:15]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 297933CycloheptylbenzeneHCID 558102Bis(dichloromethyl) etherHCID 21484447Cycloheptylbenzaldehyde

Product 1

HCID 214844454-Cycloheptyl-benzaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

Cycloheptylbenzaldehyde can be manufactured as follows: 200 ml of titanium tetrachloride are added dropwise, whilst stirring, to a solution of 200 g of cycloheptylbenzene in 600 ml of absolute methylene chloride under a nitrogen atmosphere at -10° C, and thereafter 132.5 g of dichloromethyl ether are added similarly at 0° C. The reaction mixture is then stirred for a further 30 minutes at 10° C and poured onto 3 kg of ice, and the whole is extracted twice with 500 ml of methylene chloride. The organic phases are washed with water, dried over sodium sulphate and evaporated to dryness in vacuo. Distillation of the evaporation residue in a high vacuum yields 4-cycloheptyl-benzaldehyde in the fraction boiling at 120°-130° C/0.8 mm Hg.

Workup

  1. extractionthe whole is extracted twice with 500 ml of methylene chloride
  2. washThe organic phases are washed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated to dryness in vacuo
  5. distillationDistillation of the evaporation residue in a high vacuum

Sources & evidence

ORD record
ord-f0dd31afe171456187fe90f4a2bda7de
Source dataset
uspto-grants-1977_01
Patent number
US04004026

Reaction notes

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