Oxalyl chloride → HCID 178439115, compound

HRID 342356Notes

Reaction equation

HRID 342356 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].ClC1C=CC(C2C=CC([C@H]3CC[C@H](CC[C@H]4CC[C@H](CCCCCC)CC4)CC3)=CC=2)=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].C(Cl)(=O)[C:62]([Cl:64])=[O:63]>C(Cl)Cl.O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[CH2:11][CH2:12][C@H:13]([CH2:16][CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:62]([Cl:64])=[O:63])=[CH:22][CH:23]=3)[CH2:14][CH2:15]2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 178439111HCID 178439111, compoundHCID 178443907HCID 178443907, compound

Product 1

HCID 178439115HCID 178439115, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

After 27.6 g of the (2-(trans-4-(4-n-propylphenyl)cyclohexyl)ethyl)benzene obtained in (7) of Example 2 was dissolved in 200 ml of methylene chloride, it was cooled down to 0° C., and 24 g of aluminum chloride was added to the solution and stirred. Oxalyl chloride in an amount of 22.8 g was added dropwise little by little to the solution, and after the temperature of the solution was raised up to room temperature, it was 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 20 g of 4-(2-(trans-4-(4-n-propylphenyl)cyclohexyl)ethyl)benzoyl chloride.

Workup

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

Sources & evidence

ORD record
ord-d28c547295e3482fa607c7c146d93aaa
Source dataset
uspto-grants-1999_01
Patent number
US05858275

Reaction notes

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