HCID 12140370, compound → HCID 14937397, compound

HRID 2356166Notes

Reaction equation

HRID 2356166 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][C:9]=1[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>[Pd].[Zn].O.CC(C)=O>[CH2:16]([O:15][C:9]1[CH:10]=[C:11]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[C:9]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:10]=2)[CH:12]=[CH:13][C:8]=1[O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 1

HCID 12140370HCID 12140370, compound

Product 1

HCID 14937397HCID 14937397, compoundYield 89.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23994ZincCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1200 mL of distilled water/acetone (1/1), 194 g of Pd/C (Pd: 10%), 194 g of zinc powder, and 200 g (495 mmol) of 1,2-bishexyloxy-4-iodobenzene was stirred at 50° C. for 24 hours. The resulting reaction mixture was filtered with a glass filter and extracted with chloroform. The organic phase was washed with distilled water and dried over MgSO4. Then, the solvent was evaporated and 123 g of a yellow solid was obtained. The yellow solid was recrystallized from ethanol and 58.5 g of a white solid was obtained.

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered with a glass
  3. filtrationfilter
  4. extractionextracted with chloroform
  5. washThe organic phase was washed with distilled water
  6. dry with materialdried over MgSO4
  7. customThen, the solvent was evaporated

Sources & evidence

ORD record
ord-40549fb99c5d470c993f87d10d6f8c41
Source dataset
uspto-grants-2010_07
Patent number
US07758932B2

Reaction notes

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