HCID 54287224, compound → HCID 54228915, compound

HRID 918009Notes

Reaction equation

HRID 918009 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]=[C:13]([CH3:16])[CH2:14]Br)=[CH:6][CH:5]=1>C(O)C(C)C>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]=[C:13]([CH3:16])[CH2:14][O:2][CH2:3][CH:4]([CH3:9])[CH3:5])=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 54287224HCID 54287224, compound

Product 1

HCID 54228915HCID 54228915, compound

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A solution of 6.0 g (0.02 mol) of 4-(4-bromo-3-methyl-2-butenyloxy)-benzoic methyl ester and 2.9 g (0.03 mol) of sodium-isobutylate in 130 g of isobutanol is stirred at 70° for 6 hours. After this period the reaction mixture is filtered, the filtrate is evaporated at reduced pressure. The residue is dissolved in ether, the ether solution is washed with saturated salt solution, dried with sodium sulphate and evaporated. The residue (6.5 g) is dissolved in 50 cc of absolute methanol, 0.54 g (0.01) mol of sodium methylate is added and the mixture is boiled under reflux for 2 hours. After this period 40 cc of methanol are distilled off. The remaining residue is dissolved in 100 cc of ether, the ether solution is extracted twice with 100 cc amounts of saturated salt solution and dried with sodium sulphate. The ether is distilled off and the resulting 4-(4-isobutoxy-3-methyl-2-butenyloxy)-benzoic methyl ester is purified by chromatography on silica gel with hexane/ethyl acetate 20:1. nD20 = 1.5151.

Workup

  1. filtrationAfter this period the reaction mixture is filtered
  2. customthe filtrate is evaporated at reduced pressure
  3. dissolutionThe residue is dissolved in ether
  4. washthe ether solution is washed with saturated salt solution
  5. dry with materialdried with sodium sulphate
  6. customevaporated
  7. dissolutionThe residue (6.5 g) is dissolved in 50 cc of absolute methanol
  8. addition0.54 g (0.01) mol of sodium methylate is added
  9. temperatureunder reflux for 2 hours
  10. distillationAfter this period 40 cc of methanol are distilled off
  11. dissolutionThe remaining residue is dissolved in 100 cc of ether
  12. extractionthe ether solution is extracted twice with 100 cc amounts of saturated salt solution
  13. dry with materialdried with sodium sulphate
  14. distillationThe ether is distilled off
  15. customthe resulting 4-(4-isobutoxy-3-methyl-2-butenyloxy)-benzoic methyl ester is purified by chromatography on silica gel with hexane/ethyl acetate 20:1

Sources & evidence

ORD record
ord-0b3dae75e75c4bba89bdaeafb882b6f4
Source dataset
uspto-grants-1976_07
Patent number
US03968235

Reaction notes

Loading…