Hexane → HCID 15352419, compound

HRID 1954496Notes

Reaction equation

HRID 1954496 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(Cl)Cl>[C:1]1([C:7]#[C:8][C:11]2[CH:10]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([C:8]#[C:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[C:1]([C:7]#[C:8][C:11]4[CH:10]=[CH:9][CH:14]=[CH:13][CH:12]=4)[CH:2]=3)[CH:14]=[CH:13][C:12]=2[C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8058HexaneHCID 10821Phenylacetylene

Product 1

HCID 15352419HCID 15352419, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

Analysis of the crude reaction mixture by LC at this point indicated a significant amount of unreacted starting material and products of intermediate conversion. An additional 10 g of phenylacetylene and 1 g of catalyst were added and the reaction mixture was heated at 85° C. for one hour. At this time, the LC indicated conversion was complete. The cooled reaction mixture was diluted with 500 mL of CH2Cl2 and washed with three 1-L portions of 10 percent HCl. The CH2Cl2 solution was isolated and evaporated to provide a crude solid product which was suspended in hexane. The solid was collected by filtration and purified by washing excessively with hot CCL4. This wash removeddiscoloration and many of the by-products, but it was not sufficiently effective at removing the residual Pd (II) catalyst from the monomer. The monomer was further purified by chromatography over neutral alumina using tetrahydrofuran as an eluent. The resulting monomer was isolated (32.0 g, 58 percent yield) as a light yellow solid with an m.p. of 172° C. to 174° C. with properties:

Workup

  1. customAnalysis of the crude reaction mixture by LC at this point
  2. customThe cooled reaction mixture
  3. washwashed with three 1-L portions of 10 percent HCl
  4. customThe CH2Cl2 solution was isolated
  5. customevaporated
  6. customto provide a crude solid product which
  7. filtrationThe solid was collected by filtration
  8. custompurified
  9. washby washing excessively with hot CCL4
  10. customat removing the residual Pd (II) catalyst from the monomer
  11. customThe monomer was further purified by chromatography over neutral alumina
  12. customThe resulting monomer was isolated (32.0 g, 58 percent yield) as a light yellow solid with an m.p. of 172° C. to 174° C. with properties

Sources & evidence

ORD record
ord-94a80792241848e7bdae21d8c481332f
Source dataset
uspto-grants-2000_09
Patent number
US06121495

Reaction notes

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