Potassium Hydroxide → HCID 69309430, compound

HRID 2217109Notes

Reaction equation

HRID 2217109 reaction equation
O[C:2](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5]CC)=[O:4].[OH-].[K+].S([O:27][CH2:28][C:29]1([CH2:33][CH3:34])[CH2:32][O:31][CH2:30]1)(C1C=CC(C)=CC=1)(=O)=O>C(O)C>[CH2:33]([C:29]1([CH2:28][O:27][C:12]2[CH:11]=[CH:10][C:9]([CH:8]=[CH:2][C:3]([OH:5])=[O:4])=[CH:14][CH:13]=2)[CH2:32][O:31][CH2:30]1)[CH3:34]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonateHCID 67389927HCID 67389927, compound

Product 1

HCID 69309430HCID 69309430, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

19 g of ethyl hydroxycinnamate and 7.3 g of potassium hydroxide were added to 150 ml of ethanol, and stirred at 50° C. for 1 hour. This was cooled to 40° C., and 35 g of 3-[(tosyloxy)methyl]-3-ethyloxetane was dropwise added to it. Then, this was refluxed for 3 hours. Ethanol was evaporated away, and water and toluene were added to it for liquid-liquid separation. The toluene layer was washed with 3% hydrochloric acid, saturated sodium hydrogencarbonate and water, and then toluene was evaporated away. To the resulting residue, added were 20 g of sodium hydroxide, 100 ml of ethanol and 50 ml of water, and this was refluxed for 2 hours. Ethanol was evaporated away, and the resulting residue was poured into 500 ml of 5% hydrochloric acid, and a crystal was thus formed. The crystal taken out through filtration was recrystallized from a mixed solvent of ethanol and water, and 5 g of 4-(3-ethyloxetan-3-ylmethoxy)cinnamic acid (OX6) was obtained. Its melting point was 127.5° C.

Workup

  1. temperatureThis was cooled to 40° C.
  2. temperatureThen, this was refluxed for 3 hours
  3. customEthanol was evaporated away
  4. additionwater and toluene were added to it for liquid-liquid separation
  5. washThe toluene layer was washed with 3% hydrochloric acid, saturated sodium hydrogencarbonate and water
  6. customtoluene was evaporated away
  7. additionTo the resulting residue, added
  8. temperaturethis was refluxed for 2 hours
  9. customEthanol was evaporated away
  10. additionthe resulting residue was poured into 500 ml of 5% hydrochloric acid
  11. customa crystal was thus formed
  12. filtrationThe crystal taken out through filtration
  13. customwas recrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-5d81609a713f462dade5bec9135fa841
Source dataset
uspto-grants-2008_08
Patent number
US07407691B2

Reaction notes

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