HCID 13338867, compound → Tertbutyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoate

HRID 986704Notes

Reaction equation

HRID 986704 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[Br:22])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]>ClCCl.S(=O)(=O)(O)O>[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([O:19][C:4]([CH3:24])([CH3:5])[CH3:1])=[O:18])=[CH:15][C:14]=2[Br:22])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 13338867HCID 13338867, compound

Product 1

HCID 20157032Tertbutyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoateYield 130%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoic acid (903 mg) in dichloromethane (100 ml) was added conc. sulfuric acid (five drops), and then into the mixture was bubbled isobutene under ice-cooling for 30 minutes. The mixture was left standing at room temperature for 2 days in a sealed vessel. To the reaction mixture was added sodium hydrogen carbonate, and then was bubbled nitrogen gas to remove isobutene. The insolubles were removed by filtration, and the filtrate was subjected to concentration under reduced pressure. The residue was dissolved in ethyl acetate, the solution was washed with a saturated aqueous solution of sodium hydrogen carbonate, and dried with magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was subjected to purification with silica gel flash chromatography [hexane-ethyl acetate (9:1)]. The eluate was concentrated under reduced pressure to give tertbutyl 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-bromobenzoate (660 mg) as slightly brown oily product.

Workup

  1. custominto the mixture was bubbled isobutene under ice-
  2. temperaturecooling for 30 minutes
  3. waitThe mixture was left
  4. additionTo the reaction mixture was added sodium hydrogen carbonate
  5. customwas bubbled nitrogen gas
  6. customto remove isobutene
  7. customThe insolubles were removed by filtration
  8. concentrationthe filtrate was subjected to concentration under reduced pressure
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. washthe solution was washed with a saturated aqueous solution of sodium hydrogen carbonate
  11. dry with materialdried with magnesium sulfate
  12. customThe solvent was removed by evaporation under reduced pressure
  13. customthe residue was subjected to purification with silica gel flash chromatography [hexane-ethyl acetate (9:1)]
  14. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ff76fb5786ae480a9c1b4c75f2033627
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

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