Water → HCID 21960631, compound

HRID 602227Notes

Reaction equation

HRID 602227 reaction equation
[OH-:1].[K+].CN(C)[CH:5]=[O:6].S([O:18][CH2:19][C:20]1([CH2:24][CH3:25])[CH2:23][O:22][CH2:21]1)(C1C=CC(C)=CC=1)(=O)=O.O.[C:27]1(C)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:24]([C:20]1([CH2:19][O:18][C:27]2[CH:32]=[CH:31][C:30]([C:5]([OH:6])=[O:1])=[CH:29][CH:28]=2)[CH2:21][O:22][CH2:23]1)[CH3:25]

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 21960631HCID 21960631, compound

Conditions

Temperature
70 °C

Procedure

A mixture of ethyl hydroxyl benzoate (50 g), potassium hydroxide (21 g), and dimethyl formamide (400 mL) was stirred at 70° C. for one hour. After lowering the temperature to 45° C., 3-[(tosyloxy)methyl]-3-ethyloxetane (100 g) was dropped to the reaction mixture. It was stirred for 3 hours while being kept at 45° C. Water and toluene were added and separated, and the toluene layer was washed with 3% hydrochloric acid, an aqueous saturated solution of sodium hydrogen carbonate and water. Sodium hydroxide (50 g), ethanol (500 mL) and water (200 mL) were added to residues obtained by distilling off toluene and refluxed for 2 hours. The residues obtained by distilling off ethanol were poured into 5% hydrochloric acid (500 mL) to obtain crystals. The crystals obtained by filtration were recrystallized from a solvent mixture of ethanol and water to obtain 4-(3-ethyloxetane-3-ylmethoxy)benzoic acid (OX5: 60 g). Melting point: 127.5° C.

Workup

  1. customto 45° C.
  2. stirringIt was stirred for 3 hours
  3. customwhile being kept at 45° C
  4. customseparated
  5. washthe toluene layer was washed with 3% hydrochloric acid
  6. additionSodium hydroxide (50 g), ethanol (500 mL) and water (200 mL) were added to residues
  7. customobtained
  8. distillationby distilling off toluene
  9. temperaturerefluxed for 2 hours
  10. customThe residues obtained
  11. distillationby distilling off ethanol
  12. additionwere poured into 5% hydrochloric acid (500 mL)
  13. customto obtain crystals
  14. customThe crystals obtained by filtration
  15. customwere recrystallized from a solvent mixture of ethanol and water

Sources & evidence

ORD record
ord-26dce0eba4b44cf1a0aac9dd5279abf6
Source dataset
uspto-grants-2011_03
Patent number
USRE042221E1

Reaction notes

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