Aluminum(III) Chloride → HCID 178478117, compound

HRID 486359Notes

Reaction equation

HRID 486359 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH:16]3[CH2:25][CH2:24][C:19]4([O:23][CH2:22][CH2:21][O:20]4)[CH2:18][CH2:17]3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.[H][H].[Cl-].[Al+3].[Cl-].[Cl-]>C1(C)C=CC=CC=1.C(Cl)Cl.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11]([CH2:14][CH2:15][CH:16]3[CH2:17][CH2:18][C:19]4([O:20][CH2:21][CH2:22][O:23]4)[CH2:24][CH2:25]3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 19094931HCID 19094931, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178478117HCID 178478117, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 35.0 g of 4-chloro-1-[4-(2-(1,4-dioxa-8-spiro[4.5]decyl)ethyl)-1-cyclohexenyl]benzene in 1 l of toluene is treated with 2.6 g of palladium/carbon (10%) and hydrogenated at room temperature under normal pressure until the uptake of hydrogen comes to a standstill. Thereafter, the reaction mixture is filtered and the filtrate is concentrated, there being obtained crude 4-chloro-1-[4-(2-(1,4-dioxa-8-spiro[4.5]decyl)ethyl)cyclohexyl]benzene. A suspension of 32.8 g of aluminium chloride in 215 ml of methylene chloride is treated at 18° C. while stirring and gassing with nitrogen within 10 minutes with a solution of the crude product obtained in 110 ml of methylene chloride and stirred at 0° C. for a further 30 minutes. Subsequently, the reaction mixture is poured on to 600 ml of ice/water, stirred for 10 minutes and then extracted three times with methylene chloride. The organic phases are washed in succession with water, with saturated sodium hydrogen carbonate solution and with water, then dried over sodium sulphate and filtered. Concentration of the filtrate gives 4-chloro-1-[trans-4-[2-(1,4-dioxa-8-spiro[4.5]decyl)ethyl]cyclohexyl]benzene.

Workup

  1. filtrationThereafter, the reaction mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customthere being obtained crude 4-chloro-1-[4-(2-(1,4-dioxa-8-spiro[4.5]decyl)ethyl)cyclohexyl]benzene
  4. additionis treated at 18° C.
  5. stirringstirred at 0° C. for a further 30 minutes
  6. stirringstirred for 10 minutes
  7. extractionextracted three times with methylene chloride
  8. washThe organic phases are washed in succession with water, with saturated sodium hydrogen carbonate solution and with water
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-6564d6acb7b84ada892a5bbe0544120f
Source dataset
uspto-grants-1994_03
Patent number
US05292452

Reaction notes

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