Water → HCID 178447969, compound

HRID 342360

Reaction equation

HRID 342360 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(=O)[C:29]([Cl:31])=[O:30].O>C(Cl)Cl>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=3[C:29]([Cl:31])=[O:30])[CH2:14][CH2:13]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178447967HCID 178447967, compound

Product 1

HCID 178447969HCID 178447969, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Solution prepared by dissolving 25.5 g of (trans-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)benzene in 200 ml of methylene chloride was cooled to 0° C., and 24 g of aluminum chloride was added to the solution and stirred. To the solution was added dropwise little by little 21.5 g of oxalyl chloride, and its temperature was raised to room temperature and stirred for 2 hours. After finishing of the reaction, it was added to 500 ml of water and extracted with 200 ml of methylene chloride. Organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under a reduced pressure to obtain 18 g of (trans-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)benzoylchloride.

Workup

  1. customSolution prepared
  2. temperaturewas raised to room temperature
  3. stirringstirred for 2 hours
  4. customAfter finishing of the reaction, it
  5. extractionextracted with 200 ml of methylene chloride
  6. washOrganic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-9fd01e8e4e2c4694bc2d2af4df9ed974
Source dataset
uspto-grants-1999_01
Patent number
US05858275

Linked notes

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