Dimethylformamide → HCID 21960631, compound

HRID 490022Notes

Reaction equation

HRID 490022 reaction equation
O[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[K+].CN(C)C=O.S([O:30][CH2:31][C:32]1([CH2:36][CH3:37])[CH2:35][O:34][CH2:33]1)(C1C=CC(C)=CC=1)(=O)=O>C1(C)C=CC=CC=1.O>[CH2:36]([C:32]1([CH2:31][O:30][C:11]2[CH:12]=[CH:2][C:3]([C:4]([OH:6])=[O:5])=[CH:9][CH:10]=2)[CH2:35][O:34][CH2:33]1)[CH3:37]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8365Ethyl SalicylateHCID 14797Potassium HydroxideHCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 21960631HCID 21960631, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

50 g of ethyl hydroxybenzoate and 21 g of potassium hydroxide were added to 400 mL of dimethylformamide, and stirred at 70° C. for 1 hour. After decreasing the temperature to 45° C., 100 g of 3-((tosyloxy)methyl)-3-ethyloxetane was added dropwise thereto, and then stirred at 45° C. for 3 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. 50 g of sodium hydroxide, 500 mL of ethanol and 200 mL of water were added to the resulting residue, and refluxed for 2 hours. A residue obtained by distilling ethanol off was put in 500 mL of 5% hydrochloric acid to obtain crystals. The crystals thus obtained by filtering were recrystallized from a mixed solvent of ethanol and water to obtain 60 g of 4-(3-ethyloxetane-3-ylmethoxy)benzoic acid (OX1), which had a melting point of 127.5° C.

Workup

  1. customto 45° C.
  2. stirringstirred at 45° C. for 3 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. addition50 g of sodium hydroxide, 500 mL of ethanol and 200 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 a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-20816e1ca3a541569af71e18a76e335f
Source dataset
uspto-grants-2009_05
Patent number
US07527837B2

Reaction notes

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