Ethanol → HCID 69003209, compound

HRID 490023Notes

Reaction equation

HRID 490023 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:14]([O:16]CC)=[O:15].[OH-].[K+].C(O)C.S([O:34][CH2:35][C:36]1([CH2:40][CH3:41])[CH2:39][O:38][CH2:37]1)(C1C=CC(C)=CC=1)(=O)=O>C1(C)C=CC=CC=1.O>[CH2:40]([C:36]1([CH2:35][O:34][C:7]2[CH:2]=[C:3]([C:14]([OH:16])=[O:15])[C:4]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:5][CH:6]=2)[CH2:39][O:38][CH2:37]1)[CH3:41]

Participants

7

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonateHCID 15679692HCID 15679692, compound

Product 1

HCID 69003209HCID 69003209, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

12 g of ethyl hydroxybiphenylcarboxylate and 15 g of potassium hydroxide were added to 100 mL of ethanol, and stirred at 60° C. for 1 hour. After decreasing the temperature to 45° C., 15 g of 3-((tosyloxy)methyl)-3-ethyloxetane was added dropwise thereto, and then refluxed for 2 hours. Water and toluene were added thereto, and the toluene layer was separated. The toluene layer was washed with 3% hydrochloric acid, a saturated sodium carbonate solution and water, and then toluene was distilled off. 20 g of sodium hydroxide, 500 mL of ethanol and 100 mL of water were added to the resulting residue, and refluxed for 2 hours. A residue obtained by distilling ethanol off was put in 300 mL of 5% hydrochloric acid to obtain crystals. The crystals thus obtained by filtering were recrystallized from ethanol to obtain 8 g of 4-(3-ethyloxetane-3-ylmethoxy)biphenylcarboxylic acid (OX2), which had a melting point of 222 to 225° C.

Workup

  1. customto 45° C.
  2. temperaturerefluxed for 2 hours
  3. customthe toluene layer was separated
  4. washThe toluene layer was washed with 3% hydrochloric acid
  5. distillationa saturated sodium carbonate solution and water, and then toluene was distilled off
  6. addition20 g of sodium hydroxide, 500 mL of ethanol and 100 mL of water were added to the resulting residue
  7. temperaturerefluxed for 2 hours
  8. customA residue obtained
  9. distillationby distilling ethanol
  10. customto obtain crystals
  11. customThe crystals thus obtained
  12. filtrationby filtering
  13. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-94037b1dfdaf4369bd21fbcbdaefc412
Source dataset
uspto-grants-2009_05
Patent number
US07527837B2

Reaction notes

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