Ethanol → HCID 86600972, compound

HRID 2217110Notes

Reaction equation

HRID 2217110 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9]C(OCC)=O)=[CH:4][CH:3]=1.[OH-:15].[K+].S(O[CH2:28][C:29]1([CH2:33][CH3:34])[CH2:32][O:31][CH2:30]1)(C1C=CC(C)=CC=1)(=O)=O.[CH2:35]([OH:37])C>>[CH2:33]([C:29]1([CH2:28][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]([CH3:9])[C:35]([OH:37])=[O:15])=[CH:6][CH:7]=2)[CH2:32][O:31][CH2:30]1)[CH3:34]

Participants

5

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 2736435Ethyl 4-hydroxyhydrocinnamateHCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86600972HCID 86600972, compound

Conditions

Temperature
60 °C

Procedure

17.4 g of ethyl 3-(4-hydroxyphenyl)propionate and 6.1 g of potassium hydroxide were added to 150 ml of ethanol, and stirred at 60° C. for 1 hour. This was cooled to 40° C., and 30 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)phenyl]propionic acid (OX7) was obtained. Its melting point was 85° 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-947b6c23bb5f4070815ddde55ec7c33b
Source dataset
uspto-grants-2008_08
Patent number
US07407691B2

Reaction notes

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