Benzene → HCID 178520939, compound

HRID 486361Notes

Reaction equation

HRID 486361 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:7].O.[O:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1>>[Cl:7][C:1]1[CH:6]=[CH:5][C:4]([C@H:1]2[CH2:6][CH2:5][C@H:4]([CH2:3][CH2:2][C@H:1]3[CH2:6][CH2:5][C@H:12]([CH:13]=[O:9])[CH2:11][CH2:10]3)[CH2:3][CH2:2]2)=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 962WaterHCID 8028Tetrahydrofuran

Product 1

HCID 178520939HCID 178520939, compound

Procedure

A solution of 18.1 g of 4-chloro-1-[trans-4-{2-(4-methoxymethylidene)cyclohexyl)ethyl]cyclohexyl]benzene in 90 ml of tetrahydrofuran is treated with 22.5 ml of 2N hydrochloric acid and boiled at reflux for 30 minutes while stirring and gassing with nitrogen. Subsequently, the reaction mixture is cooled to room temperature, poured into 400 ml of water and extracted with methylene chloride. The organic phases are washed with water, dried over sodium sulphate, filtered and concentrated. The residue is dissolved in 150 ml of tert.-butyl methyl ether. The solution is evaporated to a large extent and then treated with 200 ml of methanol. Crystallization at -25° C. and recrystallization of the colourless, crystalline precipitate gives pure trans-4-[2-(trans-4-(4-chlorophenyl)cyclohexyl)ethyl]cyclohexanecarboxaldehyde.

Workup

  1. temperatureat reflux for 30 minutes
  2. extractionextracted with methylene chloride
  3. washThe organic phases are washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue is dissolved in 150 ml of tert.-butyl methyl ether
  8. customThe solution is evaporated to a large extent
  9. additiontreated with 200 ml of methanol
  10. customCrystallization at -25° C.
  11. customrecrystallization of the colourless, crystalline precipitate

Sources & evidence

ORD record
ord-9337e575ad4c4b5187df8cb5c29b0182
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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