HCID 53755671, compound → 3-(4-Chlorobenzoyl)-2-methylbenzene hexanoic acid

HRID 1157008Notes

Reaction equation

HRID 1157008 reaction equation
[H][H].[Cl:3][C:4]1[CH:26]=[CH:25][C:7]([C:8]([C:10]2[C:11]([CH3:24])=[C:12]([CH2:16][CH:17]=[CH:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:6][CH:5]=1>CO.[Ni]>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10]2[C:11]([CH3:24])=[C:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 53755671HCID 53755671, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 205344893-(4-Chlorobenzoyl)-2-methylbenzene hexanoic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Hydrogen was passed through a mixture of 16.27 g of 6-[3'-(4-chlorobenzoyl)-2'-methyl-phenyl]-hex-4-enoic acid in 80 ml of methanol and 16.3 g of Raney nickel and then the catalyst was filtered off. The methoanol was distilled from the filtrate and the residue was taken up in methylene chloride. The solution was dried, treated with activated carbon, filtered and evaporated to dryness to obtain, after crystallization from a 1-1 isorpopyl ether-petroleum ether mixture, 11.15 g of 6-[3'-(4-chlorobenzoyl)-2'-methyl-phenyl]-hexanoic acid melting at 82° C.

Workup

  1. filtrationthe catalyst was filtered off
  2. distillationThe methoanol was distilled from the filtrate
  3. customThe solution was dried
  4. additiontreated with activated carbon
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto obtain
  8. customafter crystallization from a 1-1 isorpopyl ether-petroleum ether mixture, 11.15 g of 6-[3'-(4-chlorobenzoyl)-2'-methyl-phenyl]-hexanoic acid melting at 82° C.

Sources & evidence

ORD record
ord-077a4a3960cf4468a58083d413d2bbbf
Source dataset
uspto-grants-1982_06
Patent number
US04337353

Reaction notes

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