Ethanol → Ethanone, 1-(3,5-bis(phenylmethoxy)phenyl)-

HRID 1578631Notes

Reaction equation

HRID 1578631 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH:19]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=1)[C:14](OCC)=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:30](OCC)(=O)C.C(O)C>C1C=CC=CC=1.C(O)(=O)C>[CH3:30][C:14]([C:13]1[CH:12]=[C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:19]=1)=[O:15]

Participants

7

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 3016563Ethyl 3,5-bis(benzyloxy)benzoate

Product 1

HCID 120098Ethanone, 1-(3,5-bis(phenylmethoxy)phenyl)-

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent3×

Procedure

5.0 g of 50% sodium hydride suspension and a few ml of benzene were introduced in a 500 ml three-necked flask, supplied with a stirrer, reflux condenser and dropping funnel. 18.1 g of ethyl 3,5-dibenzyloxybenzoate in 150 ml of dry benzene were added. The reaction mixture was stirred and heated on an oil bath (90°-100°C.), and 4.5 g of ethyl acetate in 25 ml of dry benzene were slowly added and then heated and stirred for 7 hours. The reaction mixture was cooled. A few ml of ethanol were added and the whole was then poured into 150 ml of 50% acetic acid solution. The acidic water phase was extracted with ether. The ether phase was washed with water, sodium bicarbonate solution and water, and then dried with magnesium sulphate. After evaporation an oil was recovered. This oil was treated with 80 ml of dioxane, 16 ml of water and 8 ml of concentrated hydrochloric acid and the mixture was heated on an oil bath at 130°-140°C. for 15 hours. After evaporation, ether was added and the ether phase washed with water, 2-N sodium hydroxide solution and water. The ether phase was then evaporated and the residue was dissolved in hot ethanol and 200 ml of 1-N sodium hydroxide solution was added. The mixture was refluxed for 5 hours in order to hydrolyze remaining ethyl 3,5-dibenzyloxybenzoate. The ethanol was evaporated and the water phase extracted with ether. The ether phase was washed with water, dried with magnesium sulphate and evaporated. The remaining oil crystallized from petroleum ether (B.p. 80°-110°C.). M.p. 61.5°-62.0°C.

Workup

  1. customsupplied with a stirrer
  2. temperaturereflux condenser
  3. additionwere slowly added
  4. temperatureheated
  5. stirringstirred for 7 hours
  6. temperatureThe reaction mixture was cooled
  7. extractionThe acidic water phase was extracted with ether
  8. washThe ether phase was washed with water, sodium bicarbonate solution and water
  9. dry with materialdried with magnesium sulphate
  10. customAfter evaporation an oil
  11. customwas recovered
  12. additionThis oil was treated with 80 ml of dioxane, 16 ml of water and 8 ml of concentrated hydrochloric acid
  13. temperaturethe mixture was heated on an oil bath at 130°-140°C. for 15 hours
  14. customAfter evaporation, ether
  15. additionwas added
  16. washthe ether phase washed with water, 2-N sodium hydroxide solution and water
  17. customThe ether phase was then evaporated
  18. dissolutionthe residue was dissolved in hot ethanol
  19. addition200 ml of 1-N sodium hydroxide solution was added
  20. temperatureThe mixture was refluxed for 5 hours in order
  21. customThe ethanol was evaporated
  22. extractionthe water phase extracted with ether
  23. washThe ether phase was washed with water
  24. dry with materialdried with magnesium sulphate
  25. customevaporated
  26. customThe remaining oil crystallized from petroleum ether (B.p. 80°-110°C.)

Sources & evidence

ORD record
ord-6c39a1cf50c045729d799fd4ba77e294
Source dataset
uspto-grants-1976_02
Patent number
US03937838

Reaction notes

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