HCID 53650040, compound → 3-(4-Chlorobenzoyl)-2-methylbenzene hexanoic acid

HRID 1157009Notes

Reaction equation

HRID 1157009 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[C:9]([CH3:22])=[C:10]([CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pt]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:9]([CH3:22])=[C:10]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 53650040HCID 53650040, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 205344893-(4-Chlorobenzoyl)-2-methylbenzene hexanoic acidYield 79.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

5.425 g of 6-[3'-(4-chlorobenzoyl)-2'-methyl-phenyl]-hex-5-enoic acid dissolved in 100 ml of ethanol in the presence of 110 mg of platinum oxide had hydrogen pased therethrough and then the catalyst was filtered off. The filtrate was evaporated to dryness and the residue was taken up in ether. The solution was treated with activated carbon, filtered and evaporated to dryness. The residue was crystallized from a 1:1 isopropyl ether-petroleum ether mixture to obtain 4.34 g of 6-[3'-(4-chlorobenzoyl)-2'-methyl-phenyl]-hexanoic acid melting at 82° C.

Workup

  1. filtrationthe catalyst was filtered off
  2. customThe filtrate was evaporated to dryness
  3. additionThe solution was treated with activated carbon
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was crystallized from a 1:1 isopropyl ether-petroleum ether mixture

Sources & evidence

ORD record
ord-def883ec1ffd482b914d837b78f3bf2f
Source dataset
uspto-grants-1982_06
Patent number
US04337353

Reaction notes

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