HCID 54008758, compound → HCID 20534473, compound

HRID 1157014Notes

Reaction equation

HRID 1157014 reaction equation
[H][H].[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([C:8]([C:10]2[C:11]([CH3:27])=[C:12]([CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:6][CH:5]=1>C(O)C.[Pt]=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10]2[C:11]([CH3:27])=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])[CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 54008758HCID 54008758, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20534473HCID 20534473, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

Hydrogen was passed through a solution of 6.3 g of the acid of Step A in 100 ml of ethanol in the presence of 120 mg of platinum oxide and after the absorption of 3.86 ml of hydrogen, the mixture was filtered. The filtrate was evaporated to dryness and the 6.3 g of raw product were dissolved in 10 ml of hot isopropyl ether to which 10 ml of petroleum ether were then added. The mixture stood at room temperature, was iced and vacuum filtered. The precipitate was washed with a 1:1 isopropyl ether-petroleum ether mixture and was dried under reduced pressure to obtain 5.535 g of 9-[3'-(4-chlorobenzoyl)-2'-methyl-phenyl]-nonanoic acid melting at 64° C.

Workup

  1. customafter the absorption of 3.86 ml of hydrogen
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated to dryness
  4. dissolutionthe 6.3 g of raw product were dissolved in 10 ml of hot isopropyl ether to which 10 ml of petroleum ether
  5. additionwere then added
  6. customstood at room temperature
  7. filtrationvacuum filtered
  8. washThe precipitate was washed with a 1:1 isopropyl ether-petroleum ether mixture
  9. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-6b9e19507a24451b945b7aa02f6330e4
Source dataset
uspto-grants-1982_06
Patent number
US04337353

Reaction notes

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