P-Cresol → HCID 23047775, compound

HRID 2107140Notes

Reaction equation

HRID 2107140 reaction equation
Br[CH:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:20]1[C:25]([OH:26])=[CH:24][CH:23]=[C:22]([CH3:27])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:2]([O:26][C:25]2[CH:20]=[CH:21][C:22]([CH3:27])=[CH:23][CH:24]=2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 2879P-CresolHCID 11430Potassium CarbonateHCID 23047776HCID 23047776, compound

Product 1

HCID 23047775HCID 23047775, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5.6 g (17 mmol) of ethyl 2-bromo-7-(4-chloro-phenyl)heptanoate, 1.82 g (17 mmol) of p-cresol, 7.0 g (50 mmol) of potassium carbonate and 70 ml of butanone is heated for 36 h at the refluxing temperature. Then the inorganic precipitate is removed on a suction filter and the filtrate is concentrated. The residue is taken up in ether, the solution washed twice with 0.5N caustic soda solution, dried and concentrated by evaporation. The residual oil is chromatographed with toluene on silica gel. 5.3 g (86% of theory) is obtained of ethyl 7-(4-chloro-phenyl)-2-(4-methylphenoxy)heptanoate, a colorless oil.

Workup

  1. temperatureis heated for 36 h at the refluxing temperature
  2. customThen the inorganic precipitate is removed on a suction
  3. filtrationfilter
  4. concentrationthe filtrate is concentrated
  5. washthe solution washed twice with 0.5N caustic soda solution
  6. customdried
  7. concentrationconcentrated by evaporation
  8. customThe residual oil is chromatographed with toluene on silica gel

Sources & evidence

ORD record
ord-f4847dcb295047f596ecd13b761b9bdf
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

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