Sulfuric Acid → HCID 54354659, compound

HRID 1156180Notes

Reaction equation

HRID 1156180 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.[Mg].[Cl-].[CH2:13]([O:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])[CH3:14].S(=O)(=O)(O)O>C1C=CC=CC=1.[Cl-].[Cd+2].[Cl-]>[CH2:13]([O:15][C:16](=[O:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:23])[CH2:4][C:3]1[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:2]=1[CH3:1])[CH3:14]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 27346041-(Bromomethyl)-2,4-dimethylbenzeneHCID 5462224MagnesiumHCID 86738417HCID 86738417, compound

Product 1

HCID 54354659HCID 54354659, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 24633Cadmium chloride, dihydrateCatalystHCID 241BenzeneSolvent

Procedure

14.5 g of 2,4-dimethylbenzyl bromide, magnesium and cadmium chloride are used to prepare the corresponding cadmium-dialkyl by Huisgen's method. This compound is then reacted, in benzene solution at the boil, with 11.2 g of pimelic acid ethyl ester chloride. Sulphuric acid is added to the mixture, the organic phase is washed and the benzene is evaporated off. The residue is distilled in a high vacuum, giving 12.8 g of 8-(2,4-dimethylphenyl)-7-oxo-octanoic acid ethyl ester.

Workup

  1. washthe organic phase is washed
  2. customthe benzene is evaporated off
  3. distillationThe residue is distilled in a high vacuum

Sources & evidence

ORD record
ord-b358fc7fd22840f6a258f84de564c635
Source dataset
uspto-grants-1982_06
Patent number
US04334089

Reaction notes

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